Inventory of naturally occurring molecules bearing chiral

y-butyrolactone moiety

No. Structure Name Reference

1
0
v,::~~, 0

B$-)
Analogue of.
acetylcholine
ll

C5Hll
2 y-nonalact one 12
O e a H

3 y -caprolactone 12,21

0 y-Trityloxymethyl-
4 13
~ ~ Z HPh, 2 0 y-butyrolactone
r o
0

@
5 Podophyllotoxin 14

++'
Me0
M&
OMe

'

7 0~
<IT Me 0
'.
OMe

llb,,
OMe
,
Podorhizon

Annonacea acetogenin
15

16

8 Murisolin 17
R
Black-tailed deer
pheromone

Japaneese
beetlepherornone

Tu berolid e

Litsenilide Cl

Litsenilide C2

Valerolactone

P-hydroxy-
valerolac tone

A B ring subunit of
~reinantholideA
 Actinomy cete

Epianastrephin

Anastrephin

lsostegane

OMe

Oak lactone

Isoavenaciolide

Avenaciolide
31 Ethisolide 44
' . o+oc2b
H2C H

32

oe: Me
(+)-Dihydrocana-
densolide 47,5 1

33
H25q2vw AH t; \
HOW
Muconin 52

34
0

0'
H~~,.,.
H0
c1$25

Cinatrin C 53

35

-P
HZsCI oyy&H
21ab11,..

H0 "'* OH
Cinatrin c3 53

36 Calcidiol lactone

37
.lc,T
HO

o Trilobacin 55

CH,

38 :W:
H ~
OWIH
N CH3
~
Q u ararib ea
metabolite
56
 O p m
""H .
"''Irn3 Funebral

(+)S quamot acin

43 i 0
Corrossoline 59
OH

Stemolide
Vernolep in

Vernomenin

Precursor of CGA 8000

Paeonilactone A
54 Rosigenin 68

55
--i3
-
Sapranthin 69

56
"B H 'i.
Intermediate of
X-14547 A
(Ionophore -antibiotic)
70

Hornocitric acid
57 OTOY COOH 71
"'CH~COOH lactone

58 (+)-Digitoxigenin 72

H0 H

59
& I
Me
Ancep senolide 73

" p f H l (-)-Methylenolact-
60 74-78
ocin
'"'COOH

"Q"""
61 Protolichesterinic acid 76
"'COOH

62 (-)-Phaseolinic acid 75
 [+)-Phaseolinic acid

Lissoclinolide

r-c!

Steganone

.-gym "'"H

Frullanolide

Arbusculin
MGO

Podophyllotoxin

OMe

Picropodophyllin

(+)-Dihydroactin-
idiolide

Aeginetolide

Asteriscanolide
 Paniculide A

Enterolactone

H0
Arctigenin

OMe
OMe

Syringolide 1

Syringolide 2
 :A0
86 Hll~p~o~llb..

H0 d Secosyrin 1 104

.A0
87

d
H, , c . ~ c o ~ ~ ~ . . ,

H0
Secosyrin 2 104

88 Suributin 1 100, 104

='\ HO OCOC5H11

89 Syributin 2 100, 104

I

H0 0C0C7Hl5

Scobinolide

91 OH ~IIIIH
V Lipid metabolites 106
~ ~ 5 C ~ OAc
f

0
93 Blastirnycinone 106