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 Carbon Number

Isoprene Units

Terpene Classification

Class Name Carbon Number Monoterpene 10

Isoprene Units

Terpene Classification

Class Name Carbon Number Monoterpene 10 Sesquiterpene 15

Isoprene Units

2
3

Terpene Classification

Class Name Carbon Number Monoterpene 10 Sesquiterpene 15 Diterpene 20

Isoprene Units

2
3

Terpene Classification

Class Name Carbon Number Monoterpene 10 Sesquiterpene 15 Diterpene 20 Triterpene 30

Isoprene Units

2
3

4
6

Monoterpene Examples
CH 2OH O

Myrcene

Geraniol

a-Terpinene O

Cineole O

OH

Menthone

Menthol

Carvone

Thujone

Sesquiterpene Examples
CH 2 OH Farnesol O Eudesmol OH Bulgarene

Atractylone O

Caryophyllene O

Aromadendrene

OH Germacrone Linderene

Representative Diterpenes
CH 2 OH Phytol

COOH Pimeric acid HO O Kaurene

COOH Abietic acid

O Marrubin

Representative Triterpenes
CH 2 OH HO HO HO

Isoprene Units in Terpenes

O

Limonene

Camphor

a -Pinene

OH b -Selinene Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

a -Pinene

OH b -Selinene Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

a -Pinene

OH b -Selinene Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

a -Pinene

OH b -Selinene Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

a -Pinene

OH b -Selinene Guaiol

Non-Isoprenoid Terpenes
O

Valerane b-Vetivone

Eremophilone

Alkaloids
Nitrogen containing, basic natural products often have powerful biological activity alkaloids are not as conveniently organized by some common structural component.
Piperidine Me N

N H Pyrrolidine

N N H Pyrrolizidine Tropane

N H

Indole Quinoline NH Isoquinoline N H

Examples of alkaloids
HO N H

Coniine

O N Me

AcO

NH2

HO

Morphine

Slaframine
N MeO

HO

Quinine
N O

Strychnine
N

Me

N H MeOOC

COOMe COOMe

MeO

N H

HO

Antiobiotics
There are many classes of antibiotics; four are listed as major groups: b-lactams ( includes the penicillins); tetracyclines (tetracycline); macrolides (erythromycin) and peptides (gramacidin). For the purposes of this course, we will be primarily concerned with macrolide antibiotics and highly-oxygenated compounds.

Practice Problem #1
For each of the example terpenes given to you, find the isoprene units that are contained in the carbon skeleta.