• Terpenes• Alkaloids• Pheromones• Antibiotics

• When we discuss the terpenes we are most interested in the carbon skeleton.

Isoprene

Head

Tail

Head

Tail

Isoprene

Head

Tail

Head

Tail

Isoprene

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

CH2 OHO

O OH

O O

Myrcene Geraniol -Terpinene Cineole

Menthone Menthol Carvone Thujone

Sesquiterpene Examples

CH2OH OH

O

O O

OH

Farnesol Eudesmol Bulgarene

Atractylone Caryophyllene Aromadendrene

Germacrone Linderene

Representative Diterpenes

CH2OH

COOH COOH

O

OHO

O

Phytol

Pimeric acid Kaurene Abietic acid

Marrubin

Representative Triterpenes

HO HO HO

CH2OH

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Non-Isoprenoid Terpenes

O

Valerane

-VetivoneEremophilone

Alkaloids Nitrogen containing, basic natural products

often have powerful biological activityalkaloids are not as conveniently organized

by some common structural component.

N

HN

H

N

N

N

H

N

H

NH

Me

Pyrrolidine

Piperidine

Tropane

Pyrrolizidine

Indole

Quinoline

Isoquinoline

Examples of alkaloids

N

H

O

N

Me

HO

HO

N

AcO

NH2

N

N

O

O

N

NHO

MeO

N

H

N

MeOOC

N

H

N

Me

COOMe

HO

COOMe

MeO

Quinine

Strychnine

Morphine

Slaframine

Coniine

Vinblastine

AntiobioticsThere are many classes of antibiotics; four are listed as major groups: -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.