introduction to natural prodects

• 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 H N

H

N

N

N H

N H

NH

Me

Pyrrolidine

Piperidine

Tropane

Pyrrolizidine

IndoleQuinoline

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

NMe

COOMe

HO

COOMe

MeO

Quinine

Strychnine

MorphineSlaframine

Coniine

Vinblastine

Antiobiotics

There 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.