Intro Natural Products

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Terpenes

Alkaloids

Pheromones

Antibiotics

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When we discuss the terpenes we are mostinterested in the carbon skeleton.

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Isoprene

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Head

Tail

Head

Tail

Isoprene

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Head

Tail

Head

Tail

Isoprene

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Terpene Classification

Class Name Isoprene UnitsCarbon Number

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Terpene Classification

Class Name Isoprene UnitsCarbon Number

Monoterpene 210

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Terpene Classification

Class Name Isoprene UnitsCarbon Number

Monoterpene 210

Sesquiterpene 315

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Terpene Classification

Class Name Isoprene UnitsCarbon Number

Monoterpene 210

Sesquiterpene 315

Diterpene 420

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Terpene Classification

Class Name Isoprene UnitsCarbon Number

Monoterpene 210

Sesquiterpene 315

Diterpene 420

Triterpene 6

30

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Monoterpene Examples

CH2OH

O

O OH

O O

Myrcene Geraniol a-Terpinene Cineole

Menthone Menthol Carvone Thujone

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Sesquiterpene

Examples

CH2OHOH

O

O O

OH

Farnesol Eudesmol Bulgarene

Atractylone Cary op hy ll en e Aromadend rene

Germacrone Linderene

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RepresentativeDiterpenes

CH2OH

COOH COOH

O

OHO

O

Phytol

Pimeric acid Kaurene Abietic acid

Marrubin

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Representative

Triterpenes

HO HO HO

CH2OH

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Isoprene Units in

TerpenesO

OH

Limonene Camphor a-Pinene

b-Selinene Guaiol

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Isoprene Units in Terpenes

O

OH

Limonene Camphor a-Pinene

b-Selinene Guaiol

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Isoprene Units in Terpenes

O

OH

Limonene Camphor a-Pinene

b-Selinene Guaiol

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Isoprene Units in Terpenes

O

OH

Limonene Camphor a-Pinene

b-Selinene Guaiol

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Isoprene Units in Terpenes

O

OH

Limonene Camphor a-Pinene

b-Selinene Guaiol

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Non-Isoprenoid Terpenes

O

Valerane

b-VetivoneEremophilone

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Alkaloids

Nitrogen containing, basic natural products

often have powerful biological activityalkaloids are not as conveniently organized

by some common structural component.

NH N

H

N

N

NH

NH

NH

Me

Pyrrolidine

Piperidine

Tropane

Pyrrolizidine

Indole

Quinoline

Isoquinoline

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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

NMe

COOMe

HO

COOMe

MeO

Quinine

Strychnine

MorphineSlaframine

Coniine

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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.

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Practice Problem #1

For each of the example terpenes given toyou, find the isoprene units that are containedin the carbon skeleta.

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