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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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