Terpenes

1
Introduction to Natural Products

• Terpenes
• Alkaloids
• Pheromones
• Antibiotics

2
Terpenes

• When we discuss the terpenes we are most
  interested in the carbon skeleton.

3
Introduction to Natural Products
Isoprene
4
Introduction to Natural Products
Head
Isoprene
Tail
Head
Tail
5
Introduction to Natural Products
Head
Isoprene
Tail
Head
Tail
6
Terpene Classification

• Class Name Isoprene Units
  Carbon Number

7
Terpene Classification

• Class Name Isoprene Units
  Carbon Number
• Monoterpene 2
  10

8
Terpene Classification

• Class Name Isoprene Units
  Carbon Number
• Monoterpene 2
  10
• Sesquiterpene 3
  15

9
Terpene Classification

• Class Name Isoprene Units
  Carbon Number
• Monoterpene 2
  10
• Sesquiterpene 3
  15
• Diterpene 4
  20

10
Terpene Classification

• Class Name Isoprene Units
  Carbon Number
• Monoterpene 2
  10
• Sesquiterpene 3
  15
• Diterpene 4
  20
• Triterpene 6
  30

11
Monoterpene Examples
O
Myrcene
Geraniol
Cineole
O
O
O
OH
Menthol
Thujone
Menthone
Carvone
12
Sesquiterpene Examples
13
Representative Diterpenes
14
Representative Triterpenes
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Isoprene Units in Terpenes
O
Limonene
Camphor
OH
Guaiol
16
Isoprene Units in Terpenes
O
Limonene
Camphor
OH
Guaiol
17
Isoprene Units in Terpenes
O
Limonene
Camphor
OH
Guaiol
18
Isoprene Units in Terpenes
O
Limonene
Camphor
OH
Guaiol
19
Isoprene Units in Terpenes
O
Limonene
Camphor
OH
Guaiol
20
Non-Isoprenoid Terpenes
21
Alkaloids
Nitrogen containing, basic natural products
often have powerful biological
activity alkaloids are not as conveniently
organized by some common structural component.
22
Examples of alkaloids
23
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.
24
Practice Problem 1

• For each of the example terpenes given to you,
  find the isoprene units that are contained in the
  carbon skeleta.

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