Terpenes

Alkaloids
Pheromones
Antibiotics
 When we discuss the terpenes we are most
interested in the carbon skeleton.
Isoprene
Head
Tail Isoprene

Head

Tail
Head
Tail Isoprene

Head

Tail
 Terpene Classification

Class Name Isoprene Units

Carbon Number
 Terpene Classification

Class Name Isoprene Units

Carbon Number

Monoterpene 2
10

 Terpene Classification

Class Name Isoprene Units

Carbon Number

Monoterpene 2
10
Sesquiterpene 3
15

 Terpene Classification

Class Name Isoprene Units

Carbon Number

Monoterpene 2
10
Sesquiterpene 3
15
Diterpene 4
20

 Terpene Classification

Class Name Isoprene Units

Carbon Number

Monoterpene 2
10
Sesquiterpene 3
15
Diterpene 4
20
Triterpene 6
30
 Monoterpene
Examples
CH 2OH
O

Myrcene Geraniol -Terpinene Cineole

O O

O OH

Menthone Menthol Carvone Thujone

 Sesquiterpene
Examples
CH 2 OH OH

Farnesol Eudesmol Bulgarene

Atractylone Caryophyllene Aromadendrene

O O

OH
Germacrone Linderene
 Representative
Diterpenes
CH 2 OH

Phytol

COOH COOH
Pimericacid Kaurene Abieticacid

HO O

O
O Marrubin
 Representative
Triterpenes

CH 2 OH

HO HO HO
 Isoprene Units in
Terpenes
O

Limonene Camphor -Pinene

OH

-Selinene Guaiol
 Isoprene Units in Terpenes

Limonene Camphor Pinene

OH

Selinene Guaiol
 Isoprene Units in Terpenes

Limonene Camphor Pinene

OH

Selinene Guaiol
 Isoprene Units in Terpenes

Limonene Camphor Pinene

OH

Selinene Guaiol
 Isoprene Units in Terpenes

Limonene Camphor Pinene

OH

Selinene Guaiol
 Non-Isoprenoid
Terpenes
O

Valerane

 Alkaloids
Nitrogencontaining,basicnaturalproducts
oftenhavepowerfulbiologicalactivity
alkaloidsarenotasconvenientlyorganized
bysomecommonstructuralcomponent.
Me

Piperidine N

H
N Pyrrolizidine

Pyrrolidine H

Tropane

Indole

N
Quinoline

NH N

Isoquinoline
 HO
Examples of alkaloids

Coniine

N
Me

AcO

NH
2 HO

Morphine
HO
N

Slaframine

N MeO

Quinine

Strychnine
O

Me

H COOMe

MeOOC

COOMe

N
HO
MeO

H
 Antiobiotics
Therearemanyclassesofantibiotics;fourarelisted
asmajorgroups:lactams(includesthepenicillins);
tetracyclines(tetracycline);macrolides(erythromycin)
andpeptides(gramacidin).
Forthepurposesofthiscourse,wewillbeprimarily
concernedwithmacrolideantibiotics
andhighlyoxygenatedcompounds.
 Practice Problem #1

For each of the example terpenes given to

you, find the isoprene units that are contained
in the carbon skeleta.