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• 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.