Transcript Terpenes Alkaloids Pheromones Antibiotics

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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
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Class Name
Carbon Number
Isoprene Units
Terpene Classification
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Class Name
Carbon Number
Monoterpene
10
Isoprene Units
2
Terpene Classification
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Class Name
Carbon Number
Monoterpene
10
Sesquiterpene
15
Isoprene Units
2
3
Terpene Classification
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Class Name
Carbon Number
Monoterpene
10
Sesquiterpene
15
Diterpene
20
Isoprene Units
2
3
4
Terpene Classification
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Class Name
Carbon Number
Monoterpene
10
Sesquiterpene
15
Diterpene
20
Triterpene
30
Isoprene Units
2
3
4
6
Monoterpene Examples
CH 2OH
Myrcene
Geraniol
O
a-Terpinene
O
O
Menthone
Cineole
O
OH
Menthol
Carvone
Thujone
Sesquiterpene
Examples
OH
CH 2 OH
Farnesol
Bulgarene
Eudesmol
O
Atracty lone
Caryophy llene
Aromadendrene
O
O
OH
Germacrone
Linderene
Representative
Diterpenes
CH 2 OH
Phytol
COOH
Kaurene
Pimeric acid
HO
O
O
O
M arrubin
COOH
Abietic acid
Representative
Triterpenes
CH 2 OH
HO
HO
HO
Isoprene Units in
Terpenes
O
Limonene
a -Pinene
Camphor
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
Eremophilone
b-Vetivone
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
N
H
Pyrrolidine
N
H
Pyrrolizidine
Tropane
N
H
Indole
Quinoline
NH
Isoquinoline
N
H
Examples of alkaloids
HO
N
H
O
Coniine
N
Me
AcO
NH2
HO
N
Morphine
HO
N
Slaframine
N
MeO
N
Quinine
N
O
Strychnine
O
N
Me
N
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.