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Monoterpenoids
David H. Grayson
University Chemical Laboratory, Trinity College, Dublin 2, Ireland
Received (in Cambridge, UK) 24th February 2000
Published on the Web 22nd June 2000
Covering: mid-1997 to mid-1999. Previous review: Nat. Prod. Rep., 1998, 15, 439.
1 Introduction
2 2,6-Dimethyloctanes
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F
3 Artemisyl, santolinyl, and chrysanthemyl systems
4 Cineol derivatives
5 Menthanes
6 Pinanes
7 Camphanes and isocamphanes
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8 Caranes
9 Fenchanes
10 Thujanes
11 Ionone derivatives
12 Iridanes
13 Cannabinoids
14 References
1 Introduction
This review covers developments in monoterpenoid chemistry
which were published between mid-1997 and mid-1999, its
format being identical with that of the previous article in the
series.1
The history of terpenes and that of the Isoprene Rule have
been reviewed.2 A general review on the basics of essential oil
chemistry has appeared,3 as have reviews on the essential oils of
sage, thyme, cinnamon and wormwood.4 The monoterpenoid
constituents found in oils from members of the Annonaceae
have been discussed.5
Proposed new rules for naming the oxidation products of
monoterpenoids have been suggested, based upon the idea that
IUPAC names are unhappily “long and complex”.6 Most, if not
all, of these suggestions, examples of which include “β-caryo-
phyllon aldehyde”, “2-keto-α-myrcal” and “α-phellandradionic
acid” are likely to be of limited appeal.
The water solubilities, vapour pressures and activity
coefficients of a range of monoterpenoids have been deter-
mined,7 as have physicochemical characteristics which will be
useful in monitoring environmental concentrations and effects.8
A collection of 13C NMR data for monoterpenoids has been
published,9 and the He-1 photoelectron spectra of a number of
monoterpenoid derivatives have been measured and analysed.10
Photoacoustic spectra of essential oil vapours have been shown
to provide information which is useful in fingerprinting oils
of differing compositions.11 The mechanism of the mass-
spectrometric fragmentation of cis- and trans-rose oxides has
been investigated.12
A recommended protocol for the reproducible temperature-
programmed GC fingerprinting of essential oils using capillary
columns loaded with non-polar stationary phases has been
described,13 and the use of combination techniques such as GC-
FTIR and GC-MS in the analysis of essential oils has been
reviewed.14 The measurement by GC, as a criterion of authen-
ticity, of the enantiomeric compositions of linalool and of
DOI: 10.1039/a804437f
This journal is © The Royal Society of Chemistry 2000
linalyl acetate which are present in essential oils must be carried
out with care since it has now been shown that linalool under-
goes partial racemisation during extraction from plant material
under certain conditions.15 The use of enantioselective capillary
GC for the analysis of essential oils has been reviewed,16 and
the enantiomeric compositions of monoterpenoids present in
conifer resins have been studied.17 GC retention indexes have
been calculated for a number of monoterpenoids, and the error
of the results did not exceed an interlaboratory scattering of
experimental retention index values.18 Chemometric methods
for extracting information from analytical data on essential oils
have been described.19
The current popularity of aromatherapy, largely based upon
essential oil products, has caused some consideration to be
given to safety issues. Thus, aged, autoxidised tea-tree oil
has been shown to contain benzenoid p-cymene together with
several organic peroxides, including ascaridole which may be
linked to the occurrence of contact dermatitis.20 Phthalate
esters, currently the subject of EU legislative actions, have been
detected in citrus oils.21 Dialkyl phthalates were found in eighty-
seven citrus oils, with diisobutyl phthalate and bis(2-ethylhexyl)
phthalate occurring at concentrations up to 62 and 29.9 ppm,
respectively.
The antimicrobial properties of essential oils which are active
in the control of pathogenic bacteria and fungi have been
reviewed.22
The response of single neurons in the piriform cortex of the
rat to exposure to monoterpenoids has been studied.23
The emission of volatile monoterpenoids from plants which
is induced by grazing herbivores has been reviewed,24 as have
the effects that monoterpenoids of fodder plants exert on the
flavours of dairy products.25 Oilseed rape Brassica napus ssp.
oleifera causes seasonal respiratory symptoms amongst some
rural dwellers during its flowering season, and the major
volatile compounds which are emitted have now been identified
by thermal desorption GC-MS as being limonene, sabinene and
β-myrcene.26 A survey of some Gram-negative bacteria has
revealed that isoprene is a volatile metabolite.27 The light- and
temperature-dependence of the emission of acyclic and cyclic
monoterpenoids from Quercus ilex leaves have been studied.28 At
30 ⬚C α- and β-pinenes and sabinene are the main compounds
emitted, whereas at temperatures greater than 35 ⬚C (E)- and
(Z)-β-ocimenes are produced, reaching maximal rates at 42 ⬚C.
The emission of isoprene from leaves of Quercus alba has also
been shown to be temperature-dependent,29 and seasonal vari-
ations in the emission of isoprene from the leaves of Quercus
robur have been studied.30
Environmental effects which influence the emission of iso-
prenoids by plants have been reviewed,31 as has the biosynthesis
of these compounds.32 The reactions at low pressures of
chlorine atoms with isoprene have been investigated by
discharge-flow MS methods,33 and the formation of organic
Nat. Prod. Rep., 2000, 17, 385–419 385
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hydroperoxides and of hydrogen peroxide via the reaction of
isoprene with ozone have been studied using apparatus
designed to simulate conditions in the atmosphere.34 Method-
ology for the analysis of biogenic carbonyl compounds such as
nopinone and pinonaldehyde which arise via oxidation of
monoterpenoid alkenes in the atmosphere has been described.35
Nine species of wild mushrooms (Basidiomycetes) have been
found to produce monoterpenoids such as limonene and lin-
alool,36 and the potential of mushrooms as vehicles for the
bioproduction of monoterpenoids has been reviewed.37
General reviews on the biosynthesis of isoprenoids including
monoterpenoids have been published.38,39 It has been demon-
strated that monoterpenoid essential oil components are not
always biosynthesised via the mevalonic acid pathway, but can
be formed by another route involving glyceraldehyde-3-
phosphate and pyruvate.40,41 This pathway has been the subject
unreacted 1 then leads to the acetal 4 together with another
of several reviews.42–44 13C NMR spectroscopy has been
molecule of the potassium enolate 2.68
employed to show that the biosynthesis of bornyl acetate in the
A stereospecific synthesis of unnatural (⫹)-cis-rose oxide 5
liverwort Conocephalum conicum occurs by this route,45 and
has been described.69 Rosefuran 6 has been synthesised in 77%
isotope-labelling experiments have been used to prove that
yield via treatment of the dieneyne alcohol 7 with K2PdI4
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dimethylallyl diphosphate is not the precursor of isopentenyl

in dimethylacetamide.70 Synthetic routes to rosefuran have
diphosphate during terpenoid biosynthesis from 1-deoxy-
been reviewed,71 and a synthesis of α-clausenan 8 has been
xylulose in Catharanthus roseus.46 Secretory cells of Mentha
described.72 An efficient chemo-enzymatic route to (R)-(⫺)-
piperita which specialise in the deoxyxylulose-5-phosphate
mevalonolactone 9 has been reported.73
pathway have been isolated and yield isopentenyl diphosphate
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An antimutagenic compound from Malachra fasciata has

in the presence of an isopentenyl diphosphate isomerase inhib-
been identified 74 as the known lactone loliolide 10.
itor.47 The distribution of the mevalonate and triose phosphate
The chemistry and pharmacology of the monoterpenoid
pathways which lead to isoprenoids in a range of unicellular
indole alkaloids has been reviewed.75,76 The six novel kinabal-
algae has been examined.48
urines 11–16 have been isolated from Kopsia pauciflora,77 and
The bioengineering of monoterpenoid production,49
and factors affecting this when working with plant material 50
have been reviewed, as have the production of essential oils by
plant homogenates, plant tissue cultures and microorgan-
isms,51 and the production of monoterpenoids by Actinidia
polygama.52
A review on transformations of monoterpenoids which are
effected by microorganisms has been published.53 The synthesis
of esters of monoterpenoid alcohols via alcoholysis reactions
mediated in solvent-free systems by the lipase from Mucor mie-
hei has been studied,54 and a large number of yeasts have been
examined for their abilities to biotransform saturated and
unsaturated monoterpenoid ketones.55
GC-MS has been employed to compare essential oils which
have been obtained from plant sources by hydrodistillation and
by extraction using supercritical CO2 (SC-CO2).56 Evidence that
SC-CO2 provides oils of superior aroma qualities has been
obtained. Bitter orange oil extracted using SC-CO2 has an
odour intensity twice that of hydrodistilled material.57 A similar
comparison has been carried out on the oil which is extracted
from fruits of Coriandrum sativum,58 and the use of SC-CO2 in
the extraction of oils from Eucalyptus spp. has been reviewed.59
A modelling and simulation study of the extraction of essential
oils by SC-CO2 has been reported,60 as has a similar study of
the adsorption of monoterpenoids from SC-CO2 on to silica
gel.61 Isotherms for the adsorption of a range of monoterpen-
oids on to silanised silica from SC-CO2 have been determined.62
Reviews have been published on the reactions of mono-
terpenoids with nitrosyl chloride and uses of the products
formed,63 on peroxy-derivatives of isoprenoids including
monoterpenoids,64 on the conversion of monoterpenoid olefins
into allylic alcohols using catalytic amounts of metal salts,65 and
on the reactions of terpenoids in organised media such as when
they are encapsulated within cyclodextrins or adsorbed on to
solid catalyst surfaces.66 The behaviour of various mono-
terpenoids when they are guests within urea-linked calixarene
dimers has been described.67 incarvine D 17, methoxyincarvillateine 18, and the N-oxides 19
In an ingenious reaction cycle the silyl enol ether 1 reacts and 20 have been obtained from Incarvillea sinensis.78 Both
with catalytic amounts of potassium tert-butoxide to give the 19 and 20 were obtained as mixtures of diastereoisomers. New
potassium enolate 2 which affords the hemiacetal alkoxide 3 monoterpenoid alkaloids isolated from Osmanthus austro-
when it is treated with an aldehyde. Silyl transfer from caledonica include 79 dihydrojasminine 21 and austrodimerine

386 Nat. Prod. Rep., 2000, 17, 385–419

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Gram-positive and Gram-negative species.265 In another study,
linalool 31 was found to be the most effective component of
essential oils which possessed antibacterial action, whereas
geraniol 34 and citral 35 were more effective against a range of
yeast-like and filamentous fungi.266
The disaccharide glycosides geranyl-6-O-α--arabinofurano-
syl-β--glucopyranoside and geranyl-6-O-β--apiofuranosyl-β-
-glucopyranoside which are aroma precursors of geraniol
have been isolated 267 from flowers of Rosa damascena var.
bulgaria. Eight new geranyl disaccharide glycosides, including a
number of geranyl-3-O-α--rhamnopyranosyl-β--glucopyran-
osides have been obtained 268 from Ligustrum robustum.
A number of novel tetrol derivatives including compounds
36–39 have been isolated 269 from Foeniculum vulgare, and the

22. Five new tetrahydroisoquinoline monoterpenoid glycosides

have been obtained from Alangium lamarckii.80
The acid-catalysed deglycosylation of 8,10-dihydro-N-
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methylbakankosine 23 proceeds normally to yield the epimer-

ised aglycone 24, but the parent compound 25 affords the
rearranged product 26 via a complex mechanistic pathway
which has been subjected to a graph analysis treatment.81
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The three new hemiterpene glycosides 27–29 have been

isolated from Ilex macropoda,82 and 30 has been obtained from

saturated tetrol 40 and the epimeric pentols 41 and 42 have been

obtained 270 from Cnidium monnieri. Flowers of Tagetes minuta
contain 271 the ketones 43 and 44 together with the ketol 45. A
saponin hydrosylate of an extract of Acacia concinna has pro-
vided the menthiafolic acid derivatives 46 and 47 together with
Torillis japonica.83 A number of hemiterpene glycosides have
related glycosides.272
been found in extracts of Foeniculum vulgare.84
Plant essential oils continue to be scrutinised for their com-
ponents with a view to their economic exploitation, and Table 1
lists the principal species which have been examined during the
period under review and for which monoterpenoid constituents
have been identified and quantified.

2 2,6-Dimethyloctanes
An electroantennographic detector based on the antennae of
The new lactone β-acariolide 48 has been obtained 273 from
the Colorado beetle Leptinotarsi decemlineatha has been
the opisthonotal gland secretion of the mould mite Tyrophagus
used 262 in combination with GC-FTIR and GC-MS to investi-
putrescentiae. Novel cyclocitral and pyronene derivatives which
gate volatile organic compounds emitted by injured plants of
have been discovered include 49 and 50 from 274 Bupleurum
the potato Solanum tuberosum, and it has been confirmed that
gibraltaricum, and 51–55 from Gardenia fruits.275
several monoterpenoids, including linalool 31 and β-myrcene

32 cause prominent responses by the antennae. Insects which

feed on leaves of Gossypium hirstum cause the release of volatile
organic compounds including monoterpenoids such as (E)-β-
ocimene 33 and linalool 31 which are attractive to natural
enemies of the attacking species.263 The “spiritual and physio-
logical effects” exerted by optically active linalools 31 on young
men have been studied via sensory evaluation and brain-wave
assay methods.264 No clear conclusions have been drawn. The geranyl derivative 56 has been isolated from Piper elon-
The essential oil of Hyssopus officinalis var. decumbens is gatum Vahl.,276 and the geranyloxy compound 57 has been
rich in linalool 31 which is bactericidal against various obtained 277 from the liverwort Trichocolea hatcheri. The same

Nat. Prod. Rep., 2000, 17, 385–419 387

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Table 1 Sources of monoterpenoids

Species Principal constituents Reference

Achillea aucheri cineol, α-terpineol, α- and β-pinenes 85

Achillea chrysocoma Friv. cineol 86
Achillea corabensis (Heimerl) Micevski sabinene, p-cymene 87
Achillea eriophora DC. cineol, α- and β-pinene 88
Achillea kellalensis camphor, borneol, α-thujone, cineol, bornyl acetate, 85
camphene
Aframomum biauriculatum K. Schum monoterpenoids 89
Alpinia mutica Roxb. camphor, cineol, borneol 90
Amomum tsao-ko Crevost & Lemairs cineol, β-pinene, citral, geraniol 91
Amyris diatrypa Sprengel cineol, linalool, sabinene 92
Angelica archangelica ssp. archangelica roots: car-3-ene 93
var. norvegica (Rupr.) Rikli
Anistome antipoda γ-terpinene, terpinolene 94
Annona glabra fruits: α-pinene, limonene, 95
α-phellandrene, (E)-β-ocimene
Annona muricata cineol, linalool, α-terpineol, linalyl propionate 96
Annona squamosa peel: α- and β-pinene 97
leaf: carvone
bark: borneol, camphor
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Anthemis carpatica Willd. α-thujone, β-thujone, yomogi alcohol, terpinen-4-ol 98

Artemisia balchanorum cineol 99
Artemisia leucodes camphor 99
Artemisia rhodatha camphor 99
Artemisia roxburghiana Besser cineol, camphor, α-thujone 100
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Artemisia selengensis Turcz β-pinene, α-pinene 101

Artemisia scoparia (E)-ocimene, β-myrcene, β-pinene 102
Artemisia stolonifera Maxim cineol 101
Asterothamnus centrali-asiaticus cyclic and acyclic alkenes, artemisia ketone, 103
Novopokr. terpinen-4-ol
Bactris gasipaes limonene 104
Blepharocalyx tweediei cineol, α-terpineol 105
Blumea gariepina DC. thymyl acetate, thymol 106
Bothriochloa insculpta limonene, camphene, borneol 107
(Hochstr. ex A. Rich) A. Camus
Bothriochloa pertusa camphene, limonene, borneol, isobornyl acetate 108
Brillantaisia lamium Benth. isobornyl acetate 109
Bunium persicum (Boiss.) B. Fedtsch. fruits: p-mentha-1,4-dien-7-al, γ-terpinene, 110
β-pinene
Bupleurum gibraltarium α-pinene, β-pinene, sabinene, limonene, 111
terpinen-4-ol, trans-chrysanthemyl acetate
Cachrys ferulacea α-pinene, sabinene, limonene, chrysanthemyl acetate 112
Calaminta pamphylica ssp. davisii pulegone, menthone, menthol 113
Calaminta pamphylica ssp. pamphylica pulegone, menthyl acetate, menthol 113
Calanthe izu-insularis Ohwi et Satomi linalool 114
Calanthe sieboldii carvone 114
Callistemon citrinus (Curtis) Skeel cineol, α-pinene, α-terpineol 115
Callistemon lanceolatus DC. cineol, α-pinene, β-pinene 116
Callistemon polandii F. M. Bailey α-pinene, β-pinene, cineol, α-terpineol 116
Callistemon spp. cineol, α-pinene, limonene, α-terpineol 117
Canarium schweinfurtii Engl. monoterpene hydrocarbons, linalool 118
Canella winterana Gaertn. myrcene, linalool 119
Carissa edulis Vahl. monoterpene hydrocarbons 120
Choisya ternata Kunth α-phellandrene, myrcene 121
Chrysothamnus pulchellus β-phellandrene, (Z)-β-ocimene, (E)-β-ocimene, β-pinene 122
(Gray) Green ssp. pulchellus
Cistus ladaniferus α-pinene, bornyl acetate 123
Cistus ladaniferus var. albiflorus Dun. bornyl acetate 124
Citrus clementina sabinene, linalool, (E)-β-ocimene, terpinen-4-ol, car-3-ene, 125
limonene
Coffea arabica flowers: 2,3-epoxygeraniol, 2,3-epoxynerol, 6,7-epoxygeraniol, 126
6,7-epoxynerol
Coridothymus capitatus Rchb. carvacrol 127
Corymbia spp. α-pinene 128
Croton lanjouwensis Jablonski α-pinene, α-phellandrene, linalool 129
Crowea exalata monoterpenoids 130
Cunila menthoides Benth. isomenthone, menthone, pulegone 131
Cunila platyphylla Epling pulegone, limonene, linalool 132
Cupressus arizonica Greene α-pinene, umbellulone 133
Cupressus dupreziana α-pinene, car-3-ene 133
Cupressus glabra terpinen-4-ol, umbellulone 133
Cupressus sempervirens α-pinene, car-3-ene, α-terpinyl acetate 133
Curcuma harmandii Gagnep. cineol, α-pinene, β-pinene 134
Curcuma pierreana Gagnep. flowers: camphor, isobornyl acetate, camphene, α-pinene 135
Cymbopogon citratus citral, geraniol 136
Cymbopogon citratus Stapf. citral, myrcene 137
Cymbopogon coloratus camphene, limonene, borneol 138
Cymbopogon densiflorus Stapf. limonene, trans-p-menthadien-1-ol, verbenol, perillyl alcohol 139

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Table 1 (Contd.)

Species Principal constituents Reference

Cymbopogon giganteus p-menthadienols 136

Dendrathema indicum cineol, camphor 140
Dyssodia acerosa DC. chrysanthenone, limonene, camphor, α-pinene, sabinene, 141
camphene
Echinophora sibthorpiana Guss. α-phellandrene, car-3-ene, p-cymene, β-phellandrene 142
Echinophora spp. phellandrenes, sabinene, myrcene, p-cymene 143
Elsholtzia rugulosa Hemsl. linalool, thymol, p-menth-1(7)-en-9-ol, α-pinene 144
Ephedra intermedia 1,4-cineol 145
Ephedra sinica α-terpineol 145
Erichtites hieracifolia α-phellandrene, p-cymene, camphor, ascaridole 146
Eucalyptus alba Muell. α-pinene, β-pinene, limonene 147, 148
Eucalyptus calmadulensis Denhardt α-phellandrene, cineol, α-pinene, γ-terpinene 147
Eucalyptus citriodora citronellal, neoisopulegol, citronellol, iso(iso)pulegol 148
Eucalyptus cloeziana F. Muell. α-pinene, limonene, linalool 149
Eucalyptus curtisii β-pinene, α-pinene, (E)-β-ocimene, α-terpineol 150
Eucalyptus macarthurii Dean & Maiden geranyl acetate, gernaiol, linalool 151
Eucalyptus rubiginosa β-pinene, α-pinene, (E)-β-ocimene, α-terpineol 150
Eucalyptus tenuipes β-pinene, α-pinene, (E)-β-ocimene, α-terpineol 150
Eucalyptus spp. monoterpenoids 152–160
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Eupatorium capillifolium Small p-cymene, methyl thymol 161

Eupatorium coelestinum bornyl acetate, camphene 162
Ferulago trachycarpa (Z)-β-ocimene, myrcene 163
Flourensia cernua DC. limonene, myrcene, borneol, car-3-ene 164
Flourensia oolepsis S. L. Blake linalool 165
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Heeria insignis Del. myrcene, β-pinene, α-pinene 166

Helenium argentinum Ariza geranyl acetate, geraniol 167
Helichrysum stoechas α-pinene, limonene 168
Heterotheca latifolia Buck. borneol, camphor 169
Hippia frutescens camphor, linalool, linalyl acetate, terpinen-4-ol, α-terpineol 170
Homoranthus flavescens Cunn. ex Schauer (Z)-β-ocimene 171
Homoranthus montanus Craven & S. R. Jones (Z)-β-ocimene 171
Hypericum perforatum α-pinene, car-3-ene, myrcene 172
Hypericum scabrum α-pinene, myrcene, β-pinene 172
Hyssopus officinalis var. decumbens linalool, cineol, limonene, α-pinene, β-pinene 173
Juniperus centrasiatica Kom. α-pinene, sabinene 174
Juniperus gracilior var. urbaniana bornyl acetate, limonene, sabinene, camphene 175
Juniperus jarkendensis Kom. α-pinene, sabinene 174
Juniperus pseudosabina Fisch., α-pinene, sabinene 174
Mey. & Ave-Lall.
Juniperus sabina α-pinene, sabinene 174
Juniperus turkestanica Kom. α-pinene, sabinene 174
Kibara rigidfolia (Z )-β-ocimene, (E)-β-ocimene 176
Laserpitium petrophilum Boiss. et Heldr. α-pinene, sabinene 177
Leonitis nepetifolia linalool 178
Leptospermum coriaceum α-pinene, cineol 179
Leptospermum fastigiatum α-pinene 179
Leptospermum nitens α-pinene 179
Leptospermum spp. α-pinene 180
Leptospermum spp. α-pinene, β-pinene, cineol 181
Lippia micromeria Schauer in DC. carvacrol 182
Lomatum torreyi myrcene, β-phellandrene, (Z)-β-ocimene, (E)-β-ocimene 183
Lonicera similis Hemsl. linalool, epoxylinalool, α-terpineol 184
Melanoselinum decipiens from the Azores: limonene 185
(Schrad. & Wendl.) Hoffm. from Madeira: β-pinene
Mentha asiatica Boriss. trans-piperitone oxide, piperitenone oxide 186
Mentha grandiflora Benth. trans-piperitone oxide, piperitenone oxide, pulegone, menthone 187
Mentha longifolia ssp. petiolata trans-piperitone oxide 188
Mentha spicata trans-piperitone oxide, piperitenone oxide 189
Mentha × villoso-nervata trans-piperitone oxide 188
Micromeria dolichodontha P. H. Davis isomenthone, pulegone 190
Minthostachys setosa (Briq.) Epl. pulegone 191
Minthostachys tomentosa (Benth.) Epl. piperitone oxide 192
Minthostachys verticillata (Griseb.) Epl. pulegone, menthone 193
Monizia edulis Lowe γ-terpinene 194
Mosla chinensis Maxim thymol, carvacrol 195
Mosla punctata isopulegone, thujone 196
Myrica gale myrcene, limonene, p-cymene 197
Nepeta flavida Hub.-Mor. linalool, cineol 198
Nepeta italica cineol 199
Nepeta nuda cineol, α-terpineol 200
Nepeta spicata Benth. linalool 201
Nepeta sulfuriflora cineol, sabinene 202
Nepeta sulfuriflora P. H. Davis cineol 199
Origanum bargyli Mouterde p-cymene, carvacrol 203
Origanum boissieiri Ietswaart p-cymene, carvacrol 203
Origanum haussknechtii Boiss. p-cymene, borneol 204
Origanum husnucan-baserii borneol, α-terpineol, trans-sabinene hydrate 205

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Table 1 (Contd.)

Species Principal constituents Reference

Origanum ramonense Danin α-terpineol, terpinen-4-ol, cis-sabinene hydrate, γ-terpinene 206

Origanum tyttanthum Gontsch. carvacrol, thymol, γ-terpinene, p-cymene 207
Origanum vulgare ssp. virens linalool, (E)-β-ocimene 208
Parthenium hysterophorus geraniol 209
Passiflora edulis linalool 210
Pectis floribunda A. Rich. perillaldehyde 211
Pelargonium tomentosum Jacq. menthone, isomenthone 212
Perovskia angustifolia cineol, α-pinene, bornyl acetate, camphene, camphor, borneol 213
Perovskia scrophulariifolia cineol, camphor, bornyl acetate, p-cymene 214
Persea americana α-phellandrene 215
Phellodendron chinense Schneid. fruits: limonene, cis-limonene oxide, (⫹)-carvone 216
Pimenta racemosa (Mill) J. Moore cineol, terpinen-4-ol 217
Pinus massoniana Lamb leaf: α-pinene, β-pinene, bornyl acetate; 218
twigs: these plus β-phellandrene
Piper arboreum β-pinene 219
Piper fimbrulatum linalool, linalyl acetate 219
Pistacia integerrima Stew. ex Brandis galls: α-pinene, sabinene, β-pinene, limonene 220
bark: terpinen-4-ol, α-terpineol, α-pinene
Plectranthus barbatus α-fenchyl acetate, borneol 178
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Plectranthus sylvestris (E)-β-ocimene 178

Plectranthus vestitus Benth. flowers: cineol, neral, isobornyl acetate, geranyl acetate 221
Pleurospermum giraldii seeds: (⫺)-carvone 222
Prolium subserratum β-phellandrene, α-phellandrene 223
Pycnocycla spinosa Decne. & Boiss. linalyl acetate 224
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Rhodomyrtus canescens α-pinene, β-pinene 225

C. T. White & W. D. Francis
Rhodomyrtus pervagata Guymer α-pinene, β-pinene 225
Rhodomyrtus psidioides (G. Don.) Benth. α-pinene, limonene 225
Rhodomyrtus sericea Burret. α-pinene, β-pinene 225
Rhodomyrtus trineura ssp. capensis Guymer α-pinene 225
Rosmarinus officinalis (⫹)-verbenone 226
Salvia aytachii M. Vural et N. Adiguzel camphor, cineol 227
Salvia cedronella Boiss. cineol 228
Salvia euphratica var. euphratica trans-pinocarveyl acetate, myrtenyl acetate 229
Salvia hydrangea DC. ex Benth. cineol, α-pinene 230
Salvia pomifera ssp. pomifera α-thujone, β-thujone 231
Salvia pratensis ssp. haematodes sabinene 232
Salvia sahendica Boiss. et Buhse α-pinene, β-pinene 233
Santolina ligustica myrcene, cineol, terpinen-4-ol 234
Satureja boliviana Briq. menthone, isomenthone 235
Satureja brevicalyx Epl. menthone, isomenthone 235
Satureja brownei (Sw.) Briq. pulegone, menthone 236
Satureja icarica carvacrol 237
Satureja juliana α-pinene, β-pinene 238
Satureja pilosa carvacrol 237
Satureja punctata geranial, neral, geranyl acetate 239
Satureja pseudosimensis limonene, menthone, pulegone, piperitone oxide 178
Schinus terebinthifolius α-pinene, limonene, p-cymene 240
Simaba moiana roots: geraniol 241
Smyrnium olusatrum fruits: β-phellandrene, α-pinene 242
Solidago virgaurea α-pinene, myrcene, β-pinene, limonene, sabinene 243
Stachys corsica Pers. carvacryl acetate, linalool, α-terpinyl acetate, α-terpineol 244
Stachys glutinosa terpinen-4-ol, α-pinene, α-terpineol, β-phellandrene, γ-terpinene 245
Stachys obliqua thymol, limonene, borneol, α-pinene, isomenthol 246
Syzygium cordatum Hochst. ex Krauss limonene 247
Tagetes bipinata limonene, cis-ocimene, cis- and trans-tagetone, cis- and trans- 248
tagetenone
Tagetes minuta dihydrotagetone, (Z)-β-ocimene, (Z)-tagetone, limonene, 249
(E)-tagetone
Tagetes minuta limonene, β-phellandrene, β-ocimene, dihydrotagetone, 250
(E)-tagetone, (Z)-tagetone
Tetragastris panamensis α-pinene 223
Teucrium haenseleri Boiss. α-pinene, β-pinene 251
Thaleropia queenslandica α-pinene 252
Thymbra sintenisii Bornm. et Aznav., ssp. sintenisii carvacrol, thymol, γ-terpinene 253
Thymus atticus thymol, carvacrol, p-cymene 254
Thymus canoviridis Jalas. carvacrol, geraniol, thymol 255
Thymus jankae Chel. var. jankae linalool, geraniol, α-terpinyl acetate 256
Thymus jankae var. pantotrichus Ronn linalool, geraniol, β-pinene 256
Thymus jankae var. patentipilus Lyka linalool, geraniol, β-pinene 256
Thymus pulegioides linalool, linalyl acetate, neral, geranial, geranyl acetate, geraniol 257
Thymus roegneri thymol, carvacrol, p-cymene 252
Thymus rohlenae Velen. p-cymene, γ-terpinene 258
Trachyspermum ammi Sprague seed: carvone, limonene 259
Trinia glauca fruits: α-pinene 260
Vitex rotundifolia car-3-ene, cineol, sabinene, β-phellandrene, isoterpinolene 261

390 Nat. Prod. Rep., 2000, 17, 385–419


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species is a source of the four more highly oxidised geranyloxy
compounds 58–61. Peperomia obtusifolia has provided com-
pounds 62–64 together with the o-quinone 65.278 The unusual
oxetane 66, and compounds 67 and 68 have been found 279 in
Ethulia conyzoides. The 7-geranyloxycoumarin 69 has been
isolated from the flavedo of Citrus paradisi, and its structure
has been confirmed by synthesis.280 The compound exhibits
antifungal activity against Penicillium digitatum and P. italicum.
The chroman 70 has been extracted 281 from Peperomia clusii-
folia, the coumarin 71 has been found 282 in Piper lhotzkyanum,
View Online
and the coumarins 72 and 73 have been isolated from the root
bark of Xanthoxylum schinifolium.283
New cytotoxic geranylstilbene derivatives which have been
discovered include 74–76 from Macaranga schweinfurthii,284 and
the novel quinolone 77 from Pseudonorcardi sp. CL38489
exhibits activity against Helicobacter pylori at a concentration
of 0.1 ng mL⫺1.285 The compound is inactive against a range of
other microorganisms.
Geranylated flavonoids which have been isolated from
Dorstenia mannii include 286 compound 78, and compounds 79
and 80 have been obtained from Dorstenia poinsettifolia.287
cis-1,4-Poly-β-myrcene from the mastic resin of Pistacia
lentisus appears to be the first naturally-occurring monoterpene
polymer to have been isolated.288 The polymer possesses a
broad molecular weight distribution.
Dihydromyrcene 81 can be selectively converted under mild
conditions into dihydromyrcenol 82 or its acetate by treatment
with the Keggin-type heteropolyacid H3PW12O40 in, respec-
tively, water or acetic acid.289 A useful homoallylation of benz-
aldehyde to give 83 takes place when it is reacted with myrcene
84 in the presence of Ni(acac)2–Et3B.290 The β-zeolite-catalysed
reaction of α-methacrolein with alloocimene 85 leads to both
[4 ⫹ 2] and [3 ⫹ 2] cycloaddition products,291 and the [3 ⫹ 2]
products can be made to predominate when alkali metal ions
are present.292
High concentrations of citronellyl diphosphate 86 and of
citronellyl-β--glucoside 87, both of which are precursors
of rose oxide, have been detected in Pelargonium graveolens.293
Nat. Prod. Rep., 2000, 17, 385–419 391

(⫺)-Citronellol 88 has been converted 294 into methyl secolo-
nitoside 89.
Immobilised Candida antarctica lipase catalyses the direct
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F
formation of citronellyl acetate 90 from acetic acid and
citronella oil in a solvent-free system.295 The optimisation of
conditions for the peroxidation of citronellol 88 by 1O2 in
microemulsion systems has been discussed.296
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Citronellal 91 is cyclised to isopulegol 92 with 94% selectivity
via an intramolecular carbonyl–ene reaction which 297 is
catalysed by 5 mol% scandium triflate in CH2Cl2 at ⫺78 ⬚C. The
use of sulfated zirconia superacid catalysts for the same reac-
tion has been investigated.298 The Mo() catalysts BuEt3N⫹-
[Mo(CO)4ClBr2]⫺ and Mo(CO)5(OTf)2 also mediate the
carbonyl–ene cyclisation of citronellal but with reversal of the
usual stereoselectivity so that the product is neoisopulegol 93.299
The homochiral hydroxy-citronellal derivative 94 can also be
cyclised to afford differing product stereochemistries which
depend upon the catalyst used. Thus, with ZnBr2 the product
is (1R,3R,4R)-1-hydroxyneoisopulegol 95, whereas when
PPTS is employed (1R,3S,4R)-1-hydroxyisopulegol 96 is
formed.300
Citronellic acid 97, rarely found in nature, has been obtained
from Pelargonium papilionaceum and from P. vitifolium.301
Linalool 31 has been converted into the geranyldihydro-
chalcone 98 which is a potent 5-lipoxygenase inhibitor.302 The
tetrahydrofuran 99, derived from linalool 31, has been utilised
in a synthesis of karahanaenone 100.303
The regeneration of Pd–Al2O3 catalysts used for the hydro-
genation of dehydrolinalool 101 can be effectively carried out
by exposure to ultrasound,304 and the same hydrogenation can
be carried out over colloidal palladium catalysts which have
been formed in poly(styrene)–poly(4-vinylpyridine) micelles.305
The mesoporous molecular sieve HMCM-41 is an excellent
heterogeneous catalyst for the esterification of linalool 31 by
acetic anhydride.306
392 Nat. Prod. Rep., 2000, 17, 385–419
View Online
The enantioselective hydrolysis of rac-linalool (±)-31 by a
range of Geotrichum yeast species has been investigated.307
Geotrichum capitum CBS 0572.82 provided the best perform-
ance, but yielded (S)-linalool of only 56% ee. Tertiary esters are
not normally amenable to hydrolysis using lipases but the ester
102, which incorporates a one-carbon “spacer” group (and
which collapses after hydrolysis to propanoic acid and meth-
anal), is enantioselectively hydrolysed by Candida rugosa lipase
to afford (⫺)-linalool 31 of good ee.308 The optimum conditions
for this process involve operating in toluene at ⫺10 ⬚C.
Lime oxide-T 103 is metabolised by Glomerella cingulata to
give the acetate 104,309 and linalool 31 is converted by Asper-
gillus niger into a mixture of diastereoisomers of the alcohol 99
and of the tetrahydropyran 105.310
The regioselectivity of the hydrogenation of geraniol 34 over
platinised zeolites has been studied,311 and it has been found
that in situ mixing of [RuCl2(C6H6)]2 and the (S)-BINAP ligand
permits the enantioselective hydrogenation of 34 to give
product of 97% ee.312
The vapour phase dehydrations of geraniol 34 and of nerol
106 in the presence of zirconium phosphate and zirconium
phosphonate catalyst systems have been examined,313 and, as
expected, it has been found that nerol affords a greater percent-
age of cyclised products than does geraniol.
The reactions of geranyl chloride 107 and of linalyl chloride
108 with sodium acetate both yield linalyl acetate 109 with
96% selectivity when the reaction is catalysed by CuCl2. The
“normal” acetates are formed in the presence of triethyl-
amine.314 Geranyl chloride 107 has been converted into homo-
geranic acid 110 via conversion into digeranylbarium followed
by carbonation with CO2.315
Both geraniol 34 and nerol 106 afford the p-menthadienol
111 on treatment with tris(p-bromophenyl)ammonium hexa-
chloroantimonate followed by quenching with water.316 A
common radical cation intermediate 112 has been proposed.
Geranyl acetate 113 has been converted into the known
tetrahydrofuran 114 via hydroxylation by catalytic OsO4 in the
presence of NaIO4 in DMF.317 Neryl acetate 115 similarly
affords the diastereoisomeric product 116. For the case of
geranyl acetate, the intermediate Os() diester 117 has been
isolated and characterised. Geranyl acetate 113 undergoes
electrophilic cyclisation in the presence of Hg(OCOCF3)2 to
 View Online

3 Artemisyl, santolinyl, and chrysanthemyl systems

The novel peroxide 130 which possesses the irregular santolinyl
skeleton has been isolated from Artemisia fragrans.334

yield the products 118 and 119 after treatment with sodium
borohydride.318 α-Geranyl acetate 120 gives 121 and 122 under
the same conditions.

(±)-Lavandulol 131 is biotransformed by the plant patho-

genic fungus Glomerella cingulata to give (⫺)-132 of 100%
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The Mn-salen catalysed epoxidation reactions of geraniol 34
and of nerol 106 in the presence of hydrogen peroxide have
been studied.319 Epoxides of allylic alcohols are readily access-
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ee.335,336
A synthesis of (⫹)-lasiol 133 which is found in the mandibu-
lar gland secretion of males of the ant Lasius meridionalis has
been described,337 as have routes to (±)- and (R)-lavandulol
131,338,339 and to (±)-hotrienol 134.340 Artemisia ketone 135 has

ible in enantiomerically pure form via Sharpless asymmetric

epoxidation. In a novel transposition process, the epoxygeraniol been synthesised in 65% yield via an indium-mediated prenyl-
123 (for example) reacts with PPh3–I2–pyridine at 0 ⬚C to give ation of the dimethylacryloylpyrazole 136.341
the iodoepoxide 124 which is not isolated but which undergoes
reductive elimination to yield linalool 31 on quenching with
water.320

A synthesis from methyl 3,3-dimethylacrylate of methyl

Cultures of adventitious roots of Anthemis nobilis produce trans-chrysanthemate 137 which involves organotin chemistry
geranyl isovalerate 125, a compound which is not usually found has been described,342 as has a technical-scale preparation of
in the parent plants.321 Optimised conditions for the esterifi- the important (1R, cis, αS)-cypermethrine 138.343
cation of geraniol 34 and of citronellol 88 in solvent-free
systems by lipases from Rhizomucor miehei have been deter-
mined.322,323 Dried mycelia of Rhizopus delemar catalyse the
conversion of geraniol into its acetate by reaction with acetic
acid in heptane at 55 ⬚C.324 Product concentrations of up to 75 g
L⫺1 can be attained. A new esterase from Fusarium oxysporum
catalyses the formation of short-chain geranyl esters in organic
solvents such as hexane.325 The enzyme is used in the form
of a dry powder, and can be re-used several times without
loss of activity. Syntheses of citronellyl and geranyl esters 4 Cineol derivatives
which are catalysed by Candida rugosa lipase encapsulated in
reverse micelles have been examined but the stability of the The new hydroxycineol glycoside 139 has been isolated from the
encapsulated enzyme is low.326 fruits of Torillis japonica,83 and all four possible stereoisomers
A practical synthetic route to (E,E)-8-bromogeraniol 126 has of 2-hydroxy-1,8-cineol-β--glucopyranoside have been
been described,327 and a synthesis of (⫺)-rosiridol 127 which obtained from an aqueous extract of Foeniculum vulgare.344 The
includes an enantioselective prenyl-transfer step has been same source has provided 344 five new glycosides of 1,8-cineol
published.328 together with the five new dihydroxycineoles 140–144. The
An EXAFS study of supported Rh–Sn catalysts which are homomonoterpenoid ficusic acid 145 has been obtained from
used in the chemoselective hydrogenation of citral 35 has been Ficus macrocarpa.345
carried out.329 Selective activation of the carbonyl group may be
due to its interaction with tin oxide moieties in the bimetallic
phase. The kinetics of the hydrogenation of citral 35 over
Ni–Al2O3 which yields citronellal 91 as the primary reaction
product have been determined.330
Sporulated cultures of Penicillium digitatum convert both
geometric isomers of citral 35 into methylheptenone 128.331
γ-Pyronene 129 has been converted into safranal,332 and the
sources, uses and synthesis of geraniol 34 have been reviewed.333

Nat. Prod. Rep., 2000, 17, 385–419 393


Cineol 146 (and linalool 31) together with inorganic nitrate
can support the growth of the new Thauera strains T. terpenica
sp. nov. and T. linaloolensis sp. nov.346 The monoterpenoids are
converted into CO2 and the nitrate is reduced to dinitrogen.
The vapour–liquid equilibria at temperatures between
350–412 K for cineol 146 in the presence of (⫺)-carvone 147
have been measured.347
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5 Menthanes
The novel epoxyacetates 148 and 149 have been obtained from
Mentha rotundifolia,348 and the tetraol 150 has been isolated
from fruits of Cnidium monnieri.270 A number of menthane tri-
ols and associated glycosides have been found in Foeniculum
vulgare.349 The new (E)-5-(1-terpinen-4-olyl)-3-methoxystilbene
151 has been extracted from Alpinia katsumadai,350 and the
unusual p-menthatrienol 152 has been claimed 351 from Ligu-
laria intermedia. The carvotacetone derivatives 153–155 have
been found in Sphaeranthus suaveolens,352 and the thymols 156
and 157 are constituents of Arnica sackalinensis.353 The more
highly oxygenated compounds 158 and 159 have been found in
Carpesium lipskyi.354 New euglobal derivatives which have been
isolated from Eucalyptus grandis include euglobals G6 160 and
G7 161,355 and compound 162.356
The gas-phase basicity and proton affinity of limonene 163
have been experimentally determined, and the results agree well
394 Nat. Prod. Rep., 2000, 17, 385–419
View Online
with ab initio calculations based on density functional theory.357
The abstraction of hydrogen atoms by hydroxyl radicals from,
for example, α-phellandrene 164 or α-terpinene 165 has been
investigated.358
The selective conversion of monoterpene hydrocarbon feed-
stocks into p-cymene 166 by dehydrogenation over Pd catalysts
has been studied.359 Conversion yields of 70% are obtained
using Ce-promoted zeolite-supported catalysts, but this rises to
90% when pure silica impregnated with Pd is employed. The
β-zeolite-catalysed hydroalkoxylation of limonene 163 to give
α-terpinyl ethers 167 has been investigated using a continuous-
flow reactor system.360 Limonene 163 reacts with 4-hydroxy-
benzaldehyde over askanite-bentonite clay to give the cyclic
ether 168 in 39% yield.361
The electrocatalytic hydrogenations of limonene 163 and of
carvone 147 at a Raney nickel cathode in aqueous media pro-
ceed with much greater efficiencies when surfactants which
form micelles are substituted by those which do not.362 An
effective surfactant of this type is didodecyldimethylammonium
bromide which appears to form an interfacial film on the
electrode surface.
Processes for the conversion of limonene 163 into oxygenated
monoterpenoids have been reviewed 363 as has the chemistry of
terpinolene oxide.364 Conditions have been optimised for the
oxidation of limonene 163 by O2–PdCl2/CuCl2–LiCl in acetic
acid at 60–80 ⬚C to give mainly trans-carveyl acetate 169.365 The
oxidation of limonene 163 by O2–Co(OAc)2–NaBr affords a
wider range of products, namely the acetate 169 together with
its cis-isomer (14.8%), trans-carveol 170 (11.4%), carvone 147
(24%) and 4-acetoxy-p-mentha-1,8-diene 171 (20.6%).366 The
scope and limitations of various Pd-catalysed reactions of
limonene 163, including acetoxylation processes, have been
reviewed.367
Limonene 163 has been converted into the endoperoxide 172,
whose structure is related to that of the antimalarial yinghaosu
A. A novel thiol–oxygen co-oxidation reaction of 1,5-dienes

was used, which involves reaction with PhSH–O2 in the pres-
ence of a radical initiator followed by treatment with triphenyl-
phosphine.368 Similar reactions have been carried out with other
monoterpene dienes. Limonene 163 present in tea-tree oil from
Melaleuca alternifolia may form peroxides which can cause con-
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tact allergies.369 The oxidations of thymol 173 or of carvacrol
174 by H2O2 which are catalysed by Mn() porphyrins lead
to formation of thymoquinone 175.370 Under the same con-
ditions p-cymene 166 affords a range of products which arise
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via attack at its isopropyl group. The rearrangement reactions
of limonene epoxides which occur when they are exposed to
binary oxide catalysts have again been mentioned.371
The biosynthesis of limonene 163 and of carvone 147 in the
fruits of Carum carvi has been investigated.372 (±)-Limonene
163 affords (R)-(⫹)-α-terpineol 176 when it is metabolised by
Penicillium digitatum.373 Bioconversions of up to 45.8% have
been obtained using immobilised P. digitatum mycelia when
(R)-(⫹)-limonene is the substrate,374 and the effects which
cosolvents have on the biotransformation have been studied.375
Genes which encode a thermostable limonene hydratase have
been found in Escherichia coli.376 This permits the bacterium to
grow on limonene 163 which is biotransformed into a mixture
of α-terpineol 176, perillyl alcohol 177 and carvone 147. Micro-
somal preparations from fruits of Carum carvi which catalyse
the hydroxylation of (⫹)-limonene 163 to give (⫹)-trans-
carveol 170 have been described.377 The hydroxylation of
(⫹)-limonene 163 to trans-isopiperitenol 178 by the Hormon-
ema sp. UOFS Y-0067 has been reported.378 (⫹)-Limonene 163
is efficiently converted into perillic acid 179 by a newly-isolated
solvent-tolerant strain of Pseudomonas putida.379 Both Arxula
adeninivorans and Yarrowia lipolytica convert limonene into
perillic acid.380 In a novel microbial degradation pathway the
Rhodococcus sp. DCL14 converts limonene via its 1,2-epoxide
into the diol 180.381
Both enantiomers of rotundial 181, a mosquito repellent
which occurs naturally in Vitex rotundifolia, have been syn-
thesised from the enantiomeric limonene 1,2-epoxides.382 Oils
from two clones of Thymus vulgaris are effective against the
pathogenic plant fungi Botrytis cinerea and Rhizopus stoloni-
fer,383 and carvacrol 174 is active against the food-borne patho-
gen Bacillus cereus,384 exhibiting 100% inhibition of growth at
0.75 mmol L⫺1.
The thermochemistry of electron transfer to various per-
oxides including ascaridole 182 and its dihydro derivative has
been investigated.385
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The preparation, uses and properties of menthol 92 have
been reviewed in the context of applications to perfumery.386
The utilisation of Rh–BINAP catalysts for the commercial
asymmetric synthesis of (⫺)-menthol 92 has also been
reviewed.387 The enzymatic resolution of (±)-menthol rac-92 in
supercritical CO2 has been investigated.388
A VCD spectroscopic conformational study of (⫹)-menthol
ent-92 has been carried out.389
(⫺)-Menthol 92 is converted into its α--glucopyranoside
183 when it is incubated with lyophilised cells of Saccharomyces
cerevisiae in the presence of maltose.390 (⫺)-Menthol 92 is
converted by Cephalosporium aphidicola into a mixture of
dihydroxylated derivatives,391 and (±)-menthyl acetate 184
undergoes partial enantioselective hydrolysis with potato or
artichoke tuber pulps.392 The lipase from Candida rugosa
catalyses the formation of menthyl esters when it is encapsu-
lated within reverse micelles.326
Palladium-catalysed reaction of phenylacetylene with
(⫺)-menthol 92 and carbon monoxide affords the unsaturated
ester 185.393 The β-hydroxyselenide 186 is reduced by Li–Et2NH
to give the tetrahydrocarvol 187, probably via an intermediate
carbanion which undergoes intramolecular protonation to yield
product of the observed stereochemistry.394 Ring-opening
reactions of the chiral oxetane 188 and of its enantiomer have
been investigated.395 For example, treatment of 188 with lithium
affords the dilithio-derivative 189 which reacts with electro-
philes to give products 190.
The conjugate addition reactions of various nucleophiles
with the chiral furanone 191 have been studied.396 For instance,
reactions of 191 with diethyl malonate anion or with sodium
benzyl oxide afford the β-configured products 192. A synthesis
of the related bromofuranone 193 has been described,397 and
reaction of this with methanol in the presence of base initially
affords the enolate 194 which then reacts with 193 to give the
spiro-cyclopropane derivative 195 whose structure was deter-
mined by X-ray methods. The tandem conjugate addition–
alkylation reactions of the menthyl alkynoate 196 with R2CuLi
followed by R1CHO–Et2AlCl lead to products 197 of up to 85%
de.398 Conjugate addition of (⫺)-menthol 92 to (±)-p-
tolylvinylsulfoxide in the presence of Na–KH affords diaster-
eoisomeric adducts which can be separated by fractional crys-
tallisation to give, for example, pure 198.399 Treatment of 198
with MeI–KH then causes β-elimination to sulfoxide 199 of
100% ee. The cyclic phosphite 200, derived from (⫺)-menthol
92 and used at 1 mol% in the presence of 0.5 mol% of
copper triflate, catalyses the asymmetric conjugate addition
Nat. Prod. Rep., 2000, 17, 385–419 395

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of diethylzinc to cyclohexenone to give product of moderate
ee.400 Studies indicate that the enantioselectivity is mainly
controlled by the tartrate moiety.
A synthesis of tri-(⫺)-menthyltin hydride 201 has been
described, and its use in the stereoselective radical-initiated
reduction of the dichlorocyclopropane 202 to give optic-
ally active products has been reported.401 Reduction of the
acid chloride 203 by tributyltin hydride affords the chiral
8-phenylmenthyl glyoxalate 204.402
Asymmetric aldol reactions between benzyloxyacetaldehyde
and the ketene acetal 205 which are catalysed by the chiral
Lewis acid 206 are remarkably temperature dependent.403
Thus, at ⫺78 ⬚C the product is (⫹)-207 of 98% ee whereas at
⫺30 ⬚C (⫺)-207 of 85% ee is formed. The same Lewis acid 206
catalyses enantioselective aldol reactions of aldehydes with the
alternative ketene acetal 208.404
The chemistry and uses of α-terpineol 176 have been
reviewed,405 and the alcohol has been synthesised in optically
active form via a catalysed asymmetric Diels–Alder route.406
The hydrolysis of (±)-α-terpinyl acetate by Geotrichum yeasts
has been investigated.307
Epoxidation of the alcohol 209 under Payne’s conditions
(H2O2–CH3CN–K2CO3), a reaction which can be safely run on
a 1 kg scale, is surprisingly stereoselective, affording the cis-
epoxide 210 in >90 : 1 ratio with the trans-diastereoisomer.407
This result has been rationalised by invoking intramolecular
hydrogen-bonding of the peroxyimidic acid oxidant with the
hydroxy group of 209. α-Terpineol 176 is epoxidised with much
less cis-specificity under the same conditions.
396 Nat. Prod. Rep., 2000, 17, 385–419
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An effective procedure for the separation of perilla alcohol
177 from orange peel via solvent extraction followed by
chromatography has been described.408 Perilla alcohol 177 is
effectively oxidised to perillaldehyde 211 in an Oppenauer-like
oxidation process which is catalysed by the borinic acid
(C6F5)2BOH in the presence of pivalaldehyde.409 The procedure
is general for allylic and benzylic alcohols.
Some Mitsunobu reactions of dihydrocarveol 170 and of its
enantiomer have been investigated.410 The β-hydroxyazide 212
undergoes photolytically-induced radical fragmentation to
yield the ketonitrile 213.411 Askanite-bentonite clay catalyses
the reaction of the unsaturated alcohol 214 with salicylaldehyde
to give 215.412
The conformations of a series of menthone 216 and iso-
menthone 217 derivatives have been investigated by 1H NMR
methods and the results have been compared with those derived
via molecular modelling computations.413,414 NMR reveals that
isomenthone 217 exists in a conformational equilibrium in
which the isopropyl group is 67.5% axially orientated, whereas
calculation predicts a value of 79%.
Menthone 216 forms the lithium enolate 218 which is
diastereoselectively protonated by the chiral imide 219 to give a
19 : 81 mixture of menthone 216 and of the less thermo-
dynamically stable isomenthone 217.415 The homopolymer
obtained from methyl 5-vinylsalicylate 220 effects the diastereo-
selective protonation of the lithium enolate 221 to give a 93 : 7
mixture of the ketones 222 and 223.416
Menthone 216 has been converted into the alkynol 224 which
undergoes anionic oxy-Cope rearrangement to yield the hydra-
zulene derivative 225.417 (⫹)-Menthone ent-216 is a precursor
for the alkenol 226 which affords a carbonate ester 227 which
reacts with 4-lithioisobutylbenzene–CuI to give 228. Ozonolysis
of 228 regenerates menthone and yields (⫹)-ibuprofen 229 of
98% ee.418
The lithium enolate of (⫹)-isomenthone 217 reacts with
aldehydes to yield both diastereoisomers of the ketols 230, but
the diastereoisomeric ratio is unexpectedly influenced by the
temperature at which the reaction mixture is quenched with
water.419

(⫺)-Menthone 216 has been utilised as a “self-removing
chiral auxiliary” in a sequence where the derived unsaturated
ketols 231 are reacted with R2CuCNLi2 to yield intermediates
232 which collapse to menthone and alkylated ketones 233 of
80–90% ee.420
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The novel menthone-derived ligand 234 has been synthesised
and its behaviour studied by NMR spectroscopy. Intra-
molecular hydrogen-bonding between the phenolic and alco-
holic hydroxy groups of each “half ” of the molecule means
that rotational freedom is preserved.421 A number of chiral
calix[n]arenes 235 have been synthesised from the enantio-
merically pure ketone 236, itself obtained from (⫹)-pulegone
237 via conjugate addition of p-tert-butoxyphenylmagnesium
bromide followed by cleavage of the ether function.422 How-
ever, some epimerisation at C-4 of the menthyl system took
place during formation of the macrocycles 235.
The asymmetric epoxidation of stilbene derivatives by
dioxiranes derived from chiral monoterpenoid ketones such as
238 has been described.423
Supercooled mixtures of (⫹)- and (⫺)-carvones 147 crystal-
lise into solid solutions when they are heated.424 The association
constant for the 1 : 1 inclusion complex of (S)-(⫹)-carvone
ent-147 in β-cyclodextrin has been found to be twice that of
(R)-(⫺)-carvone 147.425
The percutaneous absorption of (⫺)-carvone 147 from
massage oils containing the ketone has been studied.426 The
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compound easily penetrates human skin, reaching peak plasma
concentrations after ca. 30 minutes. Various essential oils have
been examined for their abilities to act as fungitoxins against a
range of sugar cane pathogens, and piperitone which is prev-
alent in Lippia oil has been found to be particularly active.427
Optimum conditions for the extraction of perillaldehyde 211
from perilla oil and for its conversion into the derived anti-
oxime 239 have been described.428 This oxime, known as
perillartine, is 2000 times sweeter than sucrose.
The biosynthesis of (⫹)- and of (⫺)-carvone 147 in Mentha
cardiaca has been studied.429 A reductase obtained from
Euglena gracilis mediates the stereospecific conversion of
carvone 147 into the dihydro derivative 240.430 The biotrans-
formation of (⫺)-isopiperitenone 241 by a cell suspension
culture of Mentha piperita gives a mixture of oxygenated com-
pounds 242–244,431 and when jasmonic acid is added to the
system this acts as a signalling agent for the induction of P450
mRNA, enhancing the metabolism of the ketone substrate.432
Some biohydroxylation reactions of (⫹)-pulegone 237 have
been described.433
The hydrogenation of carvone 147 in the liquid phase over Pt
and Pt–Sn catalysts supported on alumina has been investi-
gated.434 With Pt alone the product is carvomenthone 245, but
increasing percentages of Sn favour formation of the unsatur-
ated ketone 246. Hydrogenation of (R)-carvone 147 with [(S)-
BINAP](DMF)nRuCl2–(R,R)-PhCH(NH2)CH(NH2)Ph in iso-
propanol containing KOH leads to the formation of cis-carveol
247 in quantitative yield.435 Under similar conditions, but
employing the (S,S)-diamine, (R)-pulegone 237 gives the
pulegol 248 in 97% yield. Carvone 147 is reduced to di-
hydrocarveols by sodium dithionite in toluene–water
under phase-transfer conditions.436 Details of the solvent-
dependent electrochemical reduction of pulegone 237 have
been reported.437
Carvone 147 has been converted into the silyl enol ether 249
via conjugate addition of MeMgI followed by trapping with
Me3SiCl. Mukaiyama reactions of 249 catalysed by trityl
perchlorate lead to products 250.438 The hydroformylation of
carvone 147 (and of other monoterpenoids) which is catalysed
by dinuclear thiolato-bridged Rh complexes has been
studied.439 (S)-Carvone 147 affords the aldehyde 251 selectively,
and limonene 163 is also hydroformylated at its exocyclic
double bond. Carvone 147 has been converted into the sulfide
252 which can be oxidised to the sulfone 253 using MCPBA.
Intramolecular Michael addition of the derived anion leads to
the bicyclic ketone 254 which gives the reductive elimination
product 255 on treatment with SmI2. Thus, the sulfide function
initially introduced at C-7/C-8 acts as a temporary “handle” for
Nat. Prod. Rep., 2000, 17, 385–419 397

the delivery of a nucleophile at C-6.440 Treatment of carvone
147 with the DAST–morpholine complex 256 under hyperbaric
conditions gives the gem-difluorolimonene derivative 257.441
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The synthesis of optically active insect pheromones from
monoterpenoids such as (⫹)-pulegone 237 has been
reviewed.442 The piperitenone derivatives vesperal 258 and
vesperol 259, both of (S)-configuration at C-4, have been
identified as being the female-specific semiochemicals of the
longhorn beetle Vesperus xatarti. Racemic forms of both
compounds have been synthesised.443
Carvone 147 reacts with ozone in alcoholic media to give
the diastereoisomeric peroxy-hemiacetals 260 in 50 : 50 ratio.
Treatment with catalytic amounts of sodium methoxide then
affords the keto-peroxides 261. When R is C5 or C8 the com-
pounds possess reasonable potency against the HB3 strain of
Plasmodium falciparum.444
(⫺)-Carvone 147 has been converted via a thirteen step
sequence into the lactone 262, a key intermediate in a number
of natural product syntheses,445 and (S)-(⫹)-carvone 147 has
been converted into the eremophilane sesquiterpene (R)-(⫺)-
ligularenolide.446
Enantioselective syntheses of (⫺)-mintlactone 263 and of
(⫹)-isomintlactone 264 have been described,447 and (±)-263 has
been synthesised from 4-methylcyclohexanone.448
6 Pinanes
Verbenol β--galactopyranoside 265 has been isolated from
Helminthia echioides,449 and the chrysanthenol glycosides 266
and 267 have been obtained from Erigeron linifolius.450 The two
new paeonidaninols A 268 and B 269 have been extracted from
Paeonia peregina,451 as has the related paeonidanin 270.452
A stereoselective synthesis of (7R)-paeonimetaboline I 271,
isolated from bacterial digests of Paeonia roots, has been
described,453 and paeonilactone B 272 has been synthesised
from 273 via a radical cascade sequence which is induced by its
treatment with SmI2.454
A qualitative determination of the non-volatile products
of the reaction of α-pinene 274 with hydroxyl radicals in a
398 Nat. Prod. Rep., 2000, 17, 385–419
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fast-flow reactor has been made,455 and rate constants for the
reactions of 274 with hydroxyl radicals, chlorine atoms and
chlorine radical anions have been measured.456 The oxidation
of α-pinene 274, which is a major component of emissions from
coniferous trees, by hydroxyl radicals in the presence of O2 and
NO has been studied with a view to evaluating the role of the
process in contributing to the production of trace gases in the
atmosphere.457 The gas-phase reactions of α-pinene 274 with
nitrate radicals have been found to yield α-pinene oxide 275
(60% of product mixture) and an unidentified organic nitrate
(40%).458 In the presence of oxygen the main product is cis-
pinonaldehyde 276. The reactions of cis-pinonaldehyde 276
with hydroxyl radicals in the presence of NO3 and ozone have
been investigated with a view to determining the pathway for its
degradation in the atmosphere.459
IR spectroscopy, vibrational circular dichroism (VCD),
circular polarisation Raman optical activity measurements and
Raman spectra have been utilised to investigate the vibrational
modes of the cis- and trans-pinanes 277, and of α-pinene 274
and β-pinene 278.460 The results which were obtained indicate
that VCD and Raman optical activity measurements are par-
ticularly complementary techniques. Density functional theory
has been employed to predict the vibrational absorption and
circular dichroism spectra of α-pinene 274, and this ab initio
approach has been found to be superior to Hartree–Fock SCF
calculations.461
A complete analysis of the 1H NMR spectrum of β-pinene
278 has been carried out and some earlier assignments have
been revised.462 The 1H and 13C NMR spectra of cis-myrtanol
279 and of trans-myrtanol 280 have been fully assigned, and the
validity of the assignments has been substantiated by computer
simulation of the spectra.463
An NMR method for determining the absolute configur-
ations of cyclic alkenes such as β-pinene 278 which has been
described involves their derivitisation with an axially-chiral
binaphthalene-based reagent followed by 1H NOE measure-

ments.464 The diastereomeric purities of some (1-chloro-
alkyl)boronates 281 derived from the pinane-2,3-diol 282 have
been determined by 1H NMR measurements on the 2⬘-pyridyl-
thioethers 283 formed when they are treated with 2-PySNa.465
The diastereoisomeric products possess distinguishable NMR
spectra, and the indicated intramolecular coordination from
nitrogen to boron has been proved by an X-ray structure
determination.
(⫺)-α-Pinene ent-274 is metabolised to a mixture of ver-
benone 284 and trans-verbenol 285 by the Hormonema sp.
UOFS Y-0067.378 (⫺)-β-Pinene ent-278 is oxidised by the same
microorganism to yield, initially, pinocamphone 286 which
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F
is then further metabolised to 3-hydroxypinocamphone 287.
(⫺)-cis-Myrtanol ent-279 is oxidised by Glomerella cingulata to
give 288–291 together with, extraordinarily, the thujane-7,10-
diol 292.466 However, the unconventional mechanistic scheme
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which the authors suggest for the formation of 292 does not
seem reasonable. The same species oxidises (⫹)-trans-myrtanol
280 to give 293, 294 and the carboxylic acids 295 and 296.466
(⫺)-Isopinocampheol 297 and its (⫹)-enantiomer ent-297 are
metabolised by the fungi Aspergillus niger, Rhizoctonia solani
and Glomerella cingulata.467 When G. cingulata is used, the
(⫺)-alcohol 297 is converted into a mixture of pinane-2,3-diol
282 and the diols 298 and 299, whereas (⫹)-297 affords ent-299
and the diols 300 and 301.
Metal-catalysed oxidation processes utilising either or both
of the pinanyl hydroperoxide 302 and tert-butyl hydroperoxide
have been compared.468,469 Reactions such as the Mo-catalysed
epoxidation of alkenes which involve peroxo-metal intermedi-
ates succeed only with tert-butyl hydroperoxide, but reactions
such as the Se-catalysed oxidation of alkenes to give allylic
alcohols which involve oxo-metal pathways succeed with both
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donors. Thus, pinanyl hydroperoxide 302 can be used as a probe
for distinguishing different mechanisms.
The kinetics of isomerisation of α-pinene 274 over clinipto-
lite have been studied.470 The reaction leads mainly to limonene
163 and to camphene 303, as does the liquid-phase isomeris-
ation of 274 over zeolite catalysts at 120 ⬚C.471 Conditions for
the conversion of α-pinene 274 to camphene 303 over rutile
catalysts which have been modified with sulfuric acid have been
determined.472 The hydration of α-pinene (and of camphene)
which is catalysed by US-Y zeolites in aqueous acetone at 55 ⬚C
has been studied.473 The major product is α-terpineol 176.
However, if either α-pinene 274 or β-pinene 278 are treated
with carboxylic anhydrides over US-Y zeolites the products
are fenchyl esters 304 and aryl ketones 305.474 The ester 304
(R = Et) completely inhibits the growth of Bacillus subtilis at
concentrations of 100 γ mL⫺1.
Oxidation reactions of α- and β-pinene and of camphene
mediated by the systems PdCl2–CuCl2–O2–AcOH and Pd-
(OAc)2–H2O2–AcOH have been investigated,475 as have the
autoxidation reactions of α- and β-pinene which occur in the
presence of Co(OAc)2–O2–NaBr.366
Ozonolysis of (⫺)-β-pinene 278 in the gas phase leads
to the isolable diastereoisomeric ozonides 306 which decom-
pose to yield nopinone 307 and the lactones 308 and 309.476
β-Pinene 278 has been converted into nopinone 307 in good
yield by oxidation using RuCl3–NaIO4 under phase-transfer
conditions.477
The epoxidation of a range of monoterpenoids utilising
methyltrioxorhenium CH3ReO3 as catalyst in the presence of
H2O2 and pyridine has been investigated.478 α-Pinene affords the
epoxide 275 in 90% yield under these conditions. The isomeris-
ation of the epoxide 275 over solid acid (mixed oxide) catalysts
has been studied,479 and a titanium β-zeolite has been found to
be an excellent catalyst for the rearrangement of 275 into the
important aldehyde 310.480
A stereocontrolled route to some allylmyrtenol derivatives
311 has been described,481 and (⫺)-myrtenol 312 undergoes
hydroformylation to give the tetrahydrofuran derivative 313.482
Deamination of nopylamine 314 affords a mixture of nopyl
chloride 315, nopyl acetate 316, the homomyrtenyl acetate 317
and the spirocyclopropane 318.483
Nat. Prod. Rep., 2000, 17, 385–419 399

(⫺)-α-Pinene ent-274 has been converted via the oxo-ene
alcohol 319 and its dehydration product 320 into the tetra-
hydroborinine 321. Treatment of 321 with LDA–TMEDA
affords the first enantiomerically pure chiral boratabenzene salt
322 to have been prepared.484
The bromide 323 can be converted with the benefit of ultra-
sound into its organozinc derivative, and this reacts with alde-
hydes to yield mainly γ-alkylated products 324 and with ketones
to give mainly α-alkylated products 325. The absolute con-
figuration of one of the latter has been determined by X-ray
analysis.485
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Practical methods for syntheses of (⫹)-verbenone ent-284
and of (⫹)-apoverbenone 326 from (⫹)-nopinone ent-307 have
been described.486 (⫹)-Verbenone ent-284 reacts with BF3ⴢ
Et2O–Zn(OAc)2–Ac2O to give a mixture of 327–329.487 The
known deconjugation of ent-284 using sodium hydride in THF
leads to the β,γ-unsaturated analogue 330 which reacts with
the same reagent combination at 0 ⬚C to give 331 and 332. The
latter can be converted into 331 by pyrolysis over quartz at
300 ⬚C, and reaction of 332 with K2CO3 in methanol affords
the useful chiral keto-acetate 333.487 Applications of the iso-
chrysanthenone 334 in the synthesis of chiral compounds via
rearrangement processes have been described.488
The hydroxy-sulfonamide 335 has been converted into
336 under Mitsunobu conditions,489 and photolysis of the
β-hydroxyazide 337 leads to the cyclobutane 338 in good
yield.411
400 Nat. Prod. Rep., 2000, 17, 385–419
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Uses of B-methoxydiisopinocampheylborane in asymmetric
C–C bond-forming processes have been reviewed,490 and the
hydroboronation of α-pinene 274 using diborane which is gen-
erated by the electrolysis of NaBH4 has been described.491 The
synthesis and chemistry of a number of sterically-modified
α-pinene-related 2-organylapoisopinocampheylchloro- and
-bromoboranes have been reported.492 The hydroboronations of
(⫹)-α-pinene 274 and of (⫺)-β-pinene 278 by the decaborane
complex B10H12(Me2S)2 afford chiral 6-(alkyl)-nido-B10H13
derivatives.493 Non-linear effects which occur in the reduction
of acetophenone by diisopinocampheylborane 339 have been
studied.494 The magnitudes of these effects are related to the
amount of 339 utilised to carry out the reduction.
The synthesis from (⫺)-β-pinene 278 of the chirally pure
diene 340 has been described, and its crystal and molecular
structure has been determined by X-ray analysis.495 A range of
optically active cyclopentadienyl ligands such as 341 which are
based upon the pinane skeleton have been synthesised and
converted into molybdenum carbonyl complexes.496
The bis(pinanyl) diol 342 has been prepared in optically pure
form from α-pinene of 70% ee.497 The boronates 343 have been
diastereoselectively transesterified with pinane-2,3-diol 282 to
yield products 344 whose stereochemistries have been verified
by X-ray methods.498 The boronate 345 has been converted
via 346 into B-analogues of valine which are inhibitors of
aminopeptidase enzymes.499
Nopinone 307 has been converted into a number of amino-
alcohols 347 which catalyse the enantioselective addition of
diethylzinc to aryl aldehydes to give phenylpropanol derivatives
of modest ee.500
Non-linear polarimetric behaviour of the chiral auxiliary 348
has been reported together with a cautionary note regarding the
use of [α]D measurements for the determination of ee values of
products of asymmetric synthesis reactions.501
7 Camphanes and isocamphanes
A number of novel camphane derivatives which include com-
pounds 349–351 have been isolated from the rhizomes and
roots of Glehnia littoralis.502
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The relationship between the seasonal concentrations and
compositions of volatile oils and the flammability of Juniper
ashei populations has been examined. Increased percentages of
limonene 163 increase flammability but increased percentages
of bornyl acetate 358 exert the opposite effect.516 Cultured cells
of Marchantia polymorpha suffer apoptosis when they are
exposed to monoterpenoids such as limonene, isopinocampheol
and, especially, bornyl acetate. In a defensive reaction, the cells
produce hydrogen peroxide.517
The synthesis and properties of chiral calixarenes bearing
camphorsulfonyl groups has been reviewed,518 and the novel
chiral host 359, formed via Pd-catalysed coupling of the alkynol
The crystal structure of a low-temperature phase of
(±)-camphor rac-352 has been determined with the aid of syn-
chrotron radiation.503 The values of the experimentally-deter-
mined dipole moments and rotational strengths of camphor
352, α-pinene 274 and borneol 353 have been compared with
those calculated in accordance with magnetic field perturbation
and vibronic coupling theories.504 The vibrational CD patterns
obtained were in good agreement, but the theoretically derived
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F

spectra underestimated band intensities. The intention of the

authors is to utilise these results as models for the extension of
VCD simulation techniques to larger, more complex molecules.
Substitution-induced 1H NMR chemical shifts for a number of
3-substituted camphor derivatives have been measured.505 The
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360 with 9,10-dibromoanthracene, forms a crystalline 1 : 1
inclusion complex with 1-methoxypropan-2-ol. A single recrys-
tallisation of the complex provides that alcohol in >99% ee.519

absolute configuration of (⫹)-[1-2H]ethanol has been deter-
mined to be (R) by single-crystal neutron diffraction analysis of
its ester with (⫺)-camphanic acid 354.506
The He-1 photoelectron spectra of camphor 352 and of
bromocamphor have been determined,507 and EPR spectro-
scopy has been used to discriminate between the (R)- and (S)-
forms of the anion radical derived from camphorquinone
355.508 The experiment was carried out in one of the chiral
“Softball” hosts constructed from urea-based homodimers can
accept camphor derivatives as guests,520 and the association of
camphor 352 with some other self-assembling dimeric hosts has
been studied.521
A density functional theory study of the rearrangement of
camphene hydrochloride to isobornyl chloride 361 has been
accomplished.522 The alkoxycarbonylation reactions of cam-
phene 303 (and of β-pinene 278) which occur under the influ-
ence of Pd and Sn catalysts have been investigated. Camphene
303 affords a mixture of 362–364 when MeOH–CO are
employed.523

solvents (S,S)- or (R,R)-2,3-dimethoxy-1,4-bis(dimethylamino)-

butane saturated with sodium iodide in which ion association
between the semidione and sodium ions occurs.
Density functional theory methods have been employed to
Ti() oxodichloride which is generated in situ,524 or
assign the vibrational absorption and CD spectra of camphor
SiCl4–K2CO3 utilised in chlorinated solvents 525 are reported as
352,509 and the FT-IR and FT-IR vibrational CD spectra of
being good reagents for the conversion of alcohols such as
2-vinyl-exo-borneol 356 have been compared with those
borneol 353 into the corresponding chlorides. The reaction
between K2CO3 and SiCl4 yields trichlorosiloxycarbonyl
chloride Cl3SiO2COCl which is itself a chlorinating agent, and
reaction of this with further SiCl4 gives triphosgene.
exo-2,10-Dibromobornane 365 reacts with butyllithium to
yield camphene 303, presumably via the intermediate lithio-
derivative 366.526 When the related 2-chloro 367 or 2-fluoro
368 analogues are treated with BuLi the products of initial
transmetallation can be trapped as the carboxylic acids 369
obtained for camphor.510 The CD spectra of camphor 352 and
by reaction with CO2 at low temperatures.
of its chloro-, bromo- and iodo-derivatives have been measured
in different solvents and in the gas phase.511 The solution and
gas phase spectra are very different, and the latter have been
used for comparison with calculated spectra.
A scraping of camphor 352 positioned at an air–water inter-
face “dances” spontaneously on the water surface, its motion
switching between rotation and translation. This behaviour
appears to be dependent upon the spatial heterogeneity of the
camphor layer at the interface.512,513 Not too surprisingly, the
self-motion of a camphoric acid 357 scraping at an air–water
interface has been found to be pH-dependent.514
The phase relations of camphene 303 at pressures up to 9.5 Butylstannonic acid BuSn(O)OH is a good catalyst for the
GPa and temperatures up to 1300 ⬚C have been measured.515 transesterification of delicate and reactive esters. For example,

Nat. Prod. Rep., 2000, 17, 385–419 401


methyl (E)-bromobut-4-enoate can be transesterified with iso-
borneol 370 to give the isobornyl derivative 371 in 87% yield.527
Synthetic routes to camphor 352 have been reviewed.528 The
base-catalysed nitrosation of camphor using isoamyl nitrite to
afford the anti-isomer 372 of camphorquinone mono-oxime in
a stereoselective manner has been described.529 Deprotonation
of (⫹)-camphor 352 using KH in THF gives an enolate which
reacts with Eschenmoser’s salt, CH2᎐NMe2⫹Cl⫺, to give the
endo-configured Mannich product 373. On the other hand, the
enol trimethylsilyl ether 374 reacts with the same reagent to give
the exo-product 375.530 (⫹)-Camphor 352 has been converted
into the N-formyl enamine 376 which undergoes a cyclisation
process to yield 377.531
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Synthetic approaches to taxanes which utilise (⫹)-camphor
352 as a chiral starting material have been reviewed.532 (⫹)-3,9-
Dibromocamphor 378 has been converted into the highly-
functionalised cyclopentanes 379 which are utilised as synthons
for some complex naturally-occurring antifungal agents.533 The
structures of the bromocamphorenic acids obtained via oxid-
ative rearrangement of α,α-dibromocamphor 380 have been
corrected to 381 and 382.534 9-Bromocamphor 383 has been
converted into the fragrant 9-mercaptocamphor 384 by reac-
tion with CH3COSK in NMP during three days.535 Under
the same conditions 9,10-dibromocamphor 385 reacts in
an unexpected manner via the 9,10-dithiol 386 to yield the
thioether 387 whose structure has been confirmed by X-ray
analysis. The same product 387 can be obtained from 385 by
reaction with S8 in NMP.
The dimeric ligand 388 has been synthesised and its intra-
molecular hydrogen-bonding behaviour has been studied by
NMR spectroscopy.421 The crystal and molecular structures of
the benzylcamphor dimer 389 and of its meso form have been
determined.536
The utilisation of conformationally rigid camphane deriv-
atives as tools for asymmetric synthesis continues to be
developed. A practical method has been described 537 for the
regio- and stereoselective conversion of (⫺)-camphorquinone
355 into the diol derivative 390 which is a useful chiral auxiliary.
The glyoxalate 391 is reduced by metal hydride reagents to give
402 Nat. Prod. Rep., 2000, 17, 385–419
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the α-hydroxy ester 392. Poor diastereoselectivity is observed
when sodium borohydride is used, but LiAlH(t BuO)3 at 0 ⬚C
yields (R)-configured product of >96% de, and L-SelectrideTM
at ⫺78 ⬚C affords (S)-product of similar diastereomeric
purity.538 A synthesis of the diol 393 has been reported, and the
derived α,β-unsaturated acetals 394 undergo diastereoselective
Simmons–Smith cyclopropanation reactions to give products
395 of >99% de which can be cleaved to give either optically
active aldehydes or their thioacetals with ethane-1,2-dithiol.539
The rhodium (cod) complex of the (⫹)-camphor-derived
pyridylphosphinite 396 has been prepared and assessed for its
ability to catalyse asymmetric hydroformylation reactions.
Good catalytic activity is observed but the obtained products
are of low to moderate ee.540 A theoretical study of the
asymmetric addition of diethylzinc to benzaldehyde which is
catalysed by the amino-alcohol 397 has been carried out using
MO and density functional theory calculations, and it has been
concluded that the asymmetric bias occurs because of differ-
ences in the stabilities of the four possible transition state struc-
tures.541 Syntheses of a series of new amino-alcohols derived
from (⫹)-camphor 352 and from (⫺)-fenchone 398 via their
reactions with lithiated heterocycles have been described.542 The
products catalyse the enantioselective addition of diethylzinc to
benzaldehyde in modest ee.
A good synthetic route to the imine 399, which is a pre-
cursor for the oxazolines 400, has been reported.543 The
oxazolidine 401 behaves as a chiral glyoxal equivalent, reacting
with Grignard reagents in the presence of Lewis acids to yield
diastereoisomerically pure secondary alcohols. Protection of
the newly-formed hydroxy group followed by cleavage leads to

homochiral α-hydroxy-aldehyde derivatives such as 402 which
can be further reduced to give 1,2-diols.544 The camphanoyl
aminoxyl 403 reacts with the prochiral styryl radical to give the
coupling product 404, the de of which has been determined by
1
H NMR.545 The use of camphor-derived oxazoline N-oxides
such as 405 for the enantioselective synthesis of β-hydroxy
ketones via asymmetric cycloaddition reactions with alkenes
has been reviewed.546 Acylation of the N-oxides 405 (R = Et,
Pr, etc.) leads to formation of α-acyloxyoxazolines 406 via
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diastereoselective rearrangement. The configurations of the
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new chiral centres were determined by chemical correlation
methods.547
Camphor-10-sulfonyl chloride 407 is reduced by triphenyl-
phosphine in aqueous dioxane to give the thiol 408 which is
converted by lithium aluminium hydride into the auxiliary
409.548 The derived acetal 410 acts as an ylide substrate in the
Rh2(OAc)2-catalysed asymmetric cyclopropanation of enones
by phenyldiazomethane which yields ketones 411.549
Syntheses of the unsaturated tertiary thiols 412 and 413 have
been described,550 and the solution and gas phase photochemis-
tries of some thiocamphor 414 and thiofenchone derivatives
have been studied.551 The bis-thiocamphor 415 is converted into
the 1,2-dithiine derivative 416 via a stereospecific rearrangement
when it is irradiated in the presence of iodine.552
The thioalkynes 417 and 418 have been synthesised. Com-
pound 417 undergoes an intramolecular Pauson–Khand
reaction catalysed by Co2(CO)8 to give 419 in 1.1 : 1 diastereo-
isomeric ratio, and compound 418 reacts with cyclopentene
under the same conditions to give 420 in 4.6 : 1 dr.553 Lithiation
of 1,1,2-trichloroethene with three equivalents of (Me3Si)2-
NLi followed by reaction with 421 affords the symmetrical
acetylenic dimers 422 in enantiomerically pure form. When 422
View Online
(R1 = OCH2t-Bu; R2 = H) is reacted with norbornadiene in
the presence of Co2(CO)8 the Pauson–Khand product 423 is
obtained in dr of up to 6 : 1.554
The camphorsulfonate salt 424 reacts with P4S10 to give 425
whose structure has been determined by X-ray analysis.555 A
series of hydroxy-sulfonamides 426 and 427 have been prepared
and surveyed for their abilities to catalyse the asymmetric addi-
tion of diethylzinc to aldehydes in the presence of Ti(iPrO)4.556
This paper is worthy of close attention since the authors report
a comprehensive study of the effects of temperature, solvent,
etc. on the outcome of the reactions. In a separate paper they
also report on the asymmetric addition of diethylzinc to
ketones which is catalysed by similar sulfonamides and which
occurs at ambient temperatures.557 The bis-sulfonamide 428
also catalyses the asymmetric addition of diethylzinc to alde-
hydes, including cinnamaldehyde, to yield product alcohols of
(S)-configurations and of 77–90% ee.558
The sultam 429 reacts stereoselectively with toluene-p-sulfinyl
chloride in the presence of DMAP to give the crystalline tolyl-
sulfinyl derivative 430. This reacts with Grignard reagents to
yield optically active sulfoxides 431 or with (Me3Si)2NLi to give
the chiral sulfinamide 432. The latter can be converted into
sulfinylimines 433.559
The N-acylated sultams 434 react in the presence of
[Ti(i PrO)2(η2-propene)] to give chiral bicyclo[3.1.0]hexan-1-ols
435.560 The allylated N-acylsultam 436 can be cleaved using
H2O2–Bu4NOH to give the derived carboxylic acid without
apparent racemisation. The parent sultam can be recovered
from the reaction mixture by simple filtration.561 Another non-
destructive method for removal of the auxiliary 429 from its
Nat. Prod. Rep., 2000, 17, 385–419 403
 View Online

α-substituted N-acylated derivatives involves reduction using

DIBAL which affords chiral aldehydes without any epimeris- The protected ketol 453 undergoes stereoselective aldol reac-
ation at the asymmetric carbon atom.562 tions with aldehydes to yield products 454 which can be cleaved
The crystalline diazoketone 437 reacts with alkenes R1R2C᎐᎐ using NaIO4 to give (R)-β-hydroxy acids 455.570
CH2 in the presence of catalytic Rh2(OAc)4 to give cyclopropyl
derivatives 438. The cis- and trans-isomers of 438 (R1 = t-Bu;
R2 = H) can be separated by column chromatography and the
trans-isomer recrystallised to >99% de.563 Reduction using
LiAlH4 then affords the alcohol 439, [α]D ⫺31.3.
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F

The commercially-available lactone 456 has been converted

into a series of new chiral auxiliaries 457 and 458, and
treatment of 456 with Lewis acids leads mainly to the
Diastereoselective aldol reactions of the diethylboron enolate self-aldolisation product 459.571
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440 have been investigated.564

The synthesis of the alkynoylated sultam 441 via reaction of
ent-429 with 3-trimethylsilylpropynoyl chloride in the presence
of lithium chloride has been described.565 This compound
undergoes a stereocontrolled intermolecular Pauson–Khand
reaction with norbornadiene to give 442 which can be further
processed to yield the cyclopentenone 443 of 96% ee.566

Both diastereoisomers of the bis-amide 460 have been syn-

thesised, and the compound shown catalyses the enantio-
selective addition of trimethylsilyl cyanide to benzaldehyde to
give product of 94% ee.572
A conformational study of a number of α-arylethylamides
461 of (⫺)-camphoric acid has been carried out using 1H NMR
together with MM2 calculations.573
The asymmetric fluorination of enolates utilising any of the
camphorsultam-derived reagents 444 proceeds to give products
of modest ee.567

The (camphorsulfonyl)oxaziridines 445 can be used to oxi-
dise certain 1,3-dicarbonyl compounds in an enantioselective
manner. For example, the tetralone 446 has been converted into
the ketol 447 of 95% ee via reaction of its potassium enolate by
445 (R = MeO).568
The camphor-derived diselenide 462 has been found to be the
best of a number which were surveyed for their abilities to effect
the asymmetric methoxyselenylation of alkenes. Cyclohexene
has been converted into the β-methoxyselenide 463 of 75 : 25
dr using this reagent.574 A series of chiral selenoxides 464 has

Reaction of (⫹)-10-camphorsulfonyl chloride 407 at 0 ⬚C

with iodine (5 equivalents) in the presence of triethylamine (10
equivalents) leads to a mixture of 448 (50%), 449 (16%), and the
iodoaminals 450 and 451 (7%). The major product 448 can be
oxidatively cleaved by OsO4 (cat.)–NaIO4 to give the important
aldehyde 452.569

404 Nat. Prod. Rep., 2000, 17, 385–419

 View Online
been synthesised, and 464 (Ar = p-MeO-C6H4-) protonates the
enolate 465 to give ketone of 64% ee.575 The selenuranes 466
have been prepared in optically pure form and undergo stereo-
selective reaction with hydroxide ions to yield the selenoxides
467.576 The structure of 467 (R = Ph) has been verified by X-ray
analysis, and the allylated derivatives 467 (R = CH2CH᎐᎐CR1R2)
undergo [2,3]-sigmatropic rearrangement to give products 468
which have been transformed into allylic alcohols 469 of compounds from car-3-ene 482 has been described.585 The
32–88% ee. The chlorooxaphenylselenurane 466 (X = Cl; R = carane derivatives 485 and 486 have been found to possess
Ph) reacts 577 with HgCl2 to give the Lewis acid complex 470 or acaracidal activity greater than that of N,N-diethyl-m-tolu-
with AgBF4 to give 471 whose structures were determined by amide (DEET) against the mites Tyrophagus putrescentiae and
X-ray methods. The compound 471 has been shown to be a Dermatophagoides farinae.586 The aldehyde 487 has been con-
fluoroselenurane–BF3 complex on the basis of an observed verted via the Wittig product 488 into the chiral tetrahydro-
covalent interaction between Se and one F atom. The allylic naphthalene derivative 489.587
chloroselenuranes 472 react with the carbanion derived
from phenylsulfonylacetonitrile to yield allylic selenuronium
ylides 473 which undergo diastereoselective [2,3]-sigmatropic
rearrangement to selenides 474.578
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F

Solvolysis in methanol of the dibromocarbene adduct 490

leads to a mixture of the three vinylic bromides 491–493.588
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A series of B,B-dihaloterpenylboranes has been synthesised

Aryl telluride anions displace bromide ion from 475, and
oxidation of the product using tert-BuCOCl leads to formation
of the chlorooxatelluranes 476. The chloro-substituent of 476
can be replaced by F, Br or I by treatment with the appropriate
NaX, AgX or Bu4NX salts. All of these reactions occur with
retention of configuration at Te.579 The oxatelluranes 477
react with Grignard reagents to yield enantiomerically pure
telluronium salts 478. An X-ray structure determination has
been carried out on 478 (R1 = Et; R2 = benzyl).580 The bromo-
tellurane 479 reacts similarly with methyllithium.581 A number
of enantiomerically pure spiro-telluranes 480 and spiro-selen-
uranes 481 have been synthesised and characterised.582
and surveyed in respect of their applications to enantioselective
aldol reactions. One of the best performing compounds is
494 which, via the derived ketone boron enolates, mediates the
formation of aldols of 14–74% ee and with greater than 99%
syn-stereochemistry.589
Conjugate addition of the sodium salt of diethyl phosphite
to the carenone 495 leads to the β-ketophosphonate 496.590
(⫹)-Car-3-ene 482 encapsulated in β-cyclodextrin is metabol-
ised by Acetobacter aceti to a mixture of 8-hydroxy-m-cymene
497, cis-2-hydroxycar-3-en-5-one 498 and the keto-acid 499,

amongst other products.591 The presence of the β-cyclodextrin

enhanced the stabilities of some of the products.

9 Fenchanes
Nine new glycosides, including 500 and 501, which are
derived from hydroxylated fenchones have been isolated from
8 Caranes Foeniculum vulgare.592
A comparative study of factors governing the regioselectivity
of hydrogen-abstraction processes which occur during the
autoxidations of (⫹)-car-3-ene 482 and of α-pinene 274 has
been carried out.583
(⫹)-(3,10)-Carene 483 has been synthesised from (⫹)-car-2-
ene 484,584 and the synthesis of a number of novel odoriferous

Nat. Prod. Rep., 2000, 17, 385–419 405


The He-1 photoelectron spectrum of fenchone 398 has
been recorded,507 and the CD spectrum of the ketone has been
measured both in solution and in the gas phase.511 Density func-
tional theory calculations have been used to assign the CD and
vibrational absorption spectra of fenchone.509
The thermal rearrangement of α-pinene 274 over zirconium
phosphate or phosphonate catalysts affords α-fenchene 502.313
Ritter reaction of endo-fenchyl alcohol 503 with acetonitrile
affords the amide 504 via a 6,2-endo hydride shift.593
The acetylenic alcohol 505 has been converted into the chiral
host 506 which forms a 1 : 2 complex with guest 1-methoxy-
propan-2-ol.519
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10 Thujanes
An enantioselective synthesis of (⫹)-sabinene 507 has been
described,594 and the terpene has also been obtained chemically
from (⫺)-α-thujene 508.584
(⫹)-Sabinene 507 forms an ozonide 509 which decomposes
to give the ketone 510 together with the lactones 511 and 512.476
It has been shown that sabinene 507 decomposes on the solid
GC supports Tenax A and Carboxen to give other mono-
terpene hydrocarbons and aromatic compounds.595
An enantioselective synthesis of (⫺)-α-thujone 513 has
been reported.596 The (⫹)-(R)-glyoxal derivative 514 was
used as starting material for preparation of the enyne 515
which was then converted into 516 from which 513 could be
obtained.
A European strain of the liverwort, Conocephalum conicum,
converts geranyl diphosphate into (⫺)-sabinene ent-507. The
cyclase enzyme involved has been isolated and partially puri-
fied.597 Some biohydroxylation reactions of (⫺)-α-thujone 513
have been investigated.433
406 Nat. Prod. Rep., 2000, 17, 385–419
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11 Ionone derivatives
3-Hydroxy-7,8-didehydro-β-ionol-9-O-β--glucopyranoside
517 has been isolated from rose petals,598 and the new
normegastigmane derivative 518 has been obtained from
Wahlenbergia marginata.599 4-Hydroxy-β-ionone 519 has been
found in Chloranthus spicatus.600
The sulfates 520 and 521 have been synthesised and methods
for their detection and assay developed. Both compounds were
found to be present in blueberries, 520 was found in raspberries
and 521 was found in cress.601
A synthesis of (⫺)-boscialin 522 which is a constituent of
various medicinal plants, and of its enantiomer, has been
decribed.602 The compound is active against various microbes
and against Trypanosoma brucei, and is cytotoxic against
human cancer cells. A new asymmetric synthesis of the
(⫹)-ketone 523 which is present in the essential oil from Iris
rhizomes has been published.603
The history and uses of ionone derivatives in perfumery has
been reviewed,604 as has the biosynthesis of β-damascenone
524.605 The utilisation of multilayer coil countercurrent chrom-
atography (MLCCC) for the isolation of reactive flavour pre-
cursors from Rosa damascena flowers has been reviewed.606 The
β-damascenone precursor 517 was obtained from rose petals
using this technique.
A total of 215 Streptomyces strains have been screened for
their ability to hydroxylate β-ionone 525 and/or α-ionone 526 at
C-3.607 None was found to metabolise 525 but several were able
to hydroxylate 526. Racemic α-ionone rac-526 was converted
into a mixture of (3R,6R)- and (3S,6S)-3-hydroxy-α-ionone.
Synthetic routes to enantiopure (S)- and (R)-α-ionone 526
have been optimised,608 and further new syntheses have been
described.609 The synthesis of β-ionone 525 from pseudoionone
527 can be accomplished by treating the latter with ten equiv-
alents of HF in petroleum ether containing catalytic amounts
of KF.610 Alternatively, pseudoionone 527 can be isomerised to
α-ionone 526 by treatment with trifluoroacetic acid, and 526
can then be further isomerised to β-ionone 525 by sulfuric
acid.611
The utilisation of enantioselective protonation procedures in
relation to the synthesis of (S)-(⫺)-damascone 528 has been
reviewed.612
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Ab initio calculations on the two geometrical isomers and the (⫹)-Carvone has been converted into (⫹)-dolicholactone 543
protonated form of the simple Schiff base 529 of β-ionone have and into (⫹)-alyxialactone 544 via a route 634 which utilises the
been carried out.613 The structure of the radical anion of intermediate 545.
β-ionone 525 has been studied by EPR spectroscopy and by
AM1 modelling techniques, and the rate of inversion of the
cyclohexene ring has been determined.614
The β-ionone tricarbonyliron complex 530 reacts with lithio-
acetonitrile to give only the condensation product 531, but
with lithiated ethyl acetate to give mainly the product 532 of
alternative geometry.615

The stereoselective synthesis of cyclopentanoid monoterpen-

oids has been reviewed,635 and an approach to the synthesis of
enantiomerically pure iridoid aglycones from carbohydrate-
derived precursors has been described.636 A new synthesis of
Published on 22 June 2000 on http://pubs.rsc.org | doi:10.1039/A804437F

loganin 546 has been accomplished,637 and the novel antirrhin-

olide 547, obtained from Antirrhinum majus, has also been
synthesised.638
12 Iridanes Reaction of antirrhinoside 548 with pyridine hydrochloride
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The synthesis, biosynthesis and occurrence of iridoid lactones in DMF yields both of the chlorohydrins linarioside 549 and
has been reviewed,616 as have the iridoids and secoiridoids isolinarioside 550 which can arise via stereospecific opening of
of the Gentianaceae.617 A cladistic analysis of the iridoids of the oxirane ring.639
members of the Verbenaceae has been carried out in the
context of aiding taxonomic classification.618
The biosynthesis of secologanin by Catharanthus roseus cell
cultures takes place via the triose phosphate-pyruvate pathway
rather than from mevalonic acid.619 Cell suspension cultures of
Lonicera japonica do not produce iridoid or secoiridoid glyco-
sides but are capable of converting 7-deoxyloganin into loganin
and loganin into secologanin.620
Of a number of known iridoids isolated from roots of
Verbascum thapsus, aucubin was most active in inhibiting
root elongation in pre-germinated seeds of barley Hordeum
vulgare.621
The free and glycosidically bound iridoids of Calamintha
nepeta have been studied,622 and the roles of iridoid and ionone-
derived glycosides in plants which attract and excite members Five novel trimeric secoiridoid glycosides have been obtained
of the cat family have been reviewed.623 The monoterpenoids from the dried flowers of Jasminum polyanthum which form the
which occur in the glandular trichomes of Nepeta racemosa Chinese crude drug “ye su xin”.640 The new blumeosides A–D
have been analysed. The glands were observed by cryogenic 551–554 have been isolated from Fragraea blumei G. Don.641
SEM and their contents were assayed by GC-MS. The results Blumeosides A 551 and B 552 exhibit radical-scavenging prop-
indicate that nepetalactones accumulate in these glands, and erties. The two new iridoids 555 and 556 which have been
that individual mature glands may each contain up to 30 ng of obtained from Barleria prionitis possess potent activity against
lactones.624 A nepetalactol oxido-reductase which is present respiratory syncytial virus.642
in these trichomes and which can convert cis,cis-nepeta- The novel imide linavuline 557 has been found 643 in Linaria
lactol 533 into the corresponding lactone 534 has been vulgaris.
investigated.625
A synthesis of (4S,4aR)-neonepetalactone 535 which utilises
SAMP methodology has been reported,626 as has a new route
to (±)-dihydronepetalactone 536.627 Formal total syntheses of
(±)-isodihydronepetalactone 537 628 and of (±)-mitsugashiwa-
lactone 538 628–630 have also been published. One of these
papers 630 also includes details of a synthesis of onikulactone
539. New asymmetric syntheses of (⫹)-iridomyrmecin 540 and
of its enantiomer,631 and 632 of (⫺)-isoiridomyrmecin 541 have
appeared, as has a synthesis 633 of (⫹)-isoboonein 542.

Nat. Prod. Rep., 2000, 17, 385–419 407

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Table 2 Sources of iridoids

Species Principal constituents Reference

Ajuga pyramidilis 8-acetylharpagide, harpagide 644

Allamanda cathartica known iridoids 645
Alberta magna 558 and 559 646
Aliberta sessilis known iridoids 647
Angelonia integerrima angeloside 560 648
Avicennia germinans 2⬘-(4⬙-hydroxycinnamoyl)mussaenosidic acid 649
Barleria lupulina new shanzhiside derivatives 650
Bellardia trixago known iridoids 651
Bouchea fluminensis boucheoside 561 652
Catalpae fruits 562–565 653
Cornus canadensis known iridoids 654
Crescentia cujete fruits 566–573 655
Duroia hirsuta roots duroin 574 656
Eucnide bartonioides 5-hydroxyloganin 575 657
Euphrasia pectinata boschnaloside 576, 7-hydroxyboschnaloside 577 658
Fraxinus spp. known iridoids 659
Fraxinus insularis 578 and related compounds 660
Fraxinus ornus hydroxyfraxinoside A 579, hydroxyfraxinoside B 580 661
Fraxinus oxycarba Willd. fraxicarboside A 581, fraxicarboside B 582, 662
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fraxicarboside C 583
Gardenia fruits 584 and two related compounds, 585 663
Gentiana siphonantha 586 and 587 664
Gonocaryum calleryanum 588 665
Hedyotis chrysotricha 589 and 590 666
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Hedyotis chrysotricha known iridoids 667

Hedyotis hedyotidea 591 and 592 668
Himatanthus fallax known iridoids 645
Holmskioldia sanguinea new catalpol derivatives 669
Jasminum odoratissimum five new secoiridoids 670
Jasminum polyanthum eight new secoiridoids 671
Jasminum urophyllum jasurosides E 593, F 594 and G 595 672
Lamiophlomis rotata penstemoside and acetylshanzhiside derivatives 673
Linaria purpurea purpureoside 596 674
Lippia graveolens caryoptosidic acid 597, lippioside I 598, lippioside II 599 675
Lisianthius seemannii seemannoside A 600 676
Loasa acerifolia loasafolioside 601 677
Loasa acerifolia asaolaside 602 678
Loasa acerifolia Dombey acerifolioside 603, tricoloroside methyl ester 604 679
Marrubium alysson 1,5,9-epideoxyloganic acid 605 680
Nepeta cadmea 1,5,9-epideoxyloganic acid glucosyl ester 681
Nepeta cadmea Boiss. nepetalactone 682
Nepeta grandiflora 1,5,9-epideoxyloganic acid derivatives 683
Pedicularis artselaeri artselaenin I 606, artselaenin II 607, artselaenin III 608 684, 685
Pedicularis musicola Maxim. known iridoids 686
Pedicularis procera proceroside 609 687
Pedicularis grandiflorus 5,6β-dihydroxyadoxoside 610 688
Pedicularis mucronatus (5αH )-6α-hydroxy-8-epihydrocornin 611, 689
(5αH )-6α-hydroxy-8-epiloganin 612
Penstemon secundiflorus 5,6β-dihydroxyadoxoside 610 688
Penstemon secundiflorus 10-hydroxy-(5αH )-6-epidihydrocornin 613 690
Picconia excelsa picconioside I 614 691
Picrorhiza scrophularii piccroside IV 615 692
Plumeria alba known iridoids 693
Premna subscandens acylated globularinin and globularimin derivatives 694
Premna subscandens acylated catalpol derivatives 695
Scaevola floribunda floribundal 616 696
Scrophularia auriculata scrovalentinoside 697
ssp. pseudoauriculata
Scrophularia leucoclada harpagide, 8-O-acetylharpagide 698
Scrophularia ningpoensis harpagide and harpagoside derivatives 699
Scrophularia scorodonica known catalpol derivatives 700
Tecoma capensis 7-O-(p-methoxybenzoyl)tecomoside 617 701
Tocoyena bullata gardenoside 702
Tocoyena formosa formosinoside 618 703
Verbascum spinosum verbaspinoside 704
Verbascum undulosum 619 705
Verbenoxylum retzii 2⬘-apiosylgardoside 706
Veronica bellidioides 6⬘-O-menthiafoloylmussaenosidic acid 620 707
Viburnum ayavacense suspensolide derivatives 708
Viticis trifoliae viteoid I 621, viteoid II 622 709

As usual, many plants have been screened for the presence of obtained, with structural formulae being provided wherever
new and previously described iridoids during the period under this appears most appropriate.
review. Table 2 lists the principal substances which have been

408 Nat. Prod. Rep., 2000, 17, 385–419

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Nat. Prod. Rep., 2000, 17, 385–419

409
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13 Cannabinoids
A synthesis of ent-∆1-tetrahydrocannabinol 623 has been
described,710 and the synthetic diol 624 shows a lower affinity
for cannabinoid receptors than does ∆8-tetrahydrocannab-
inol.711 The isomeric 1⬘-, 2⬘- and 3⬘-methylheptyl-∆8-tetra-
hydrocannabinols 625 have been synthesised and shown to
be more potent than ∆8-THC.712 All four diastereoisomers
of 1⬘,2⬘-dimethylheptyl-∆8-tetrahydrocannabinol 626 have
also been synthesised, and the (1⬘R,2⬘S)- and (1S,2⬘R)-
compounds exhibit the highest potencies.713 11-Hydroxy-
(1⬘S,2⬘R)-dimethylheptyl-∆8-tetrahydrocannabinol 627 has
been prepared, and pharmacological studies show that it is one
of the most potent traditional cannabinoids known.714

410 Nat. Prod. Rep., 2000, 17, 385–419


The bifunctional cannabinoid (±)-628 has been syn-
thesised,715 and routes to racemic and optically active forms
of 11-nor-∆9-tetrahydrocannabinol-9-carboxylic acid 629, the
major urinary metabolite of ∆9-tetrahydrocannabinol, have
been reported. The starting ketone 630 was resolved via its
diastereoisomeric acetals with (⫹)-diisopropyl tartrate.716
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