Chemistry of

Natural Products

‫ محمد ربيع‬.‫د‬
‫المحاضرة الثالثة‬
 Or

Norbornane Pinane
Thujane Carane
 C C C
C C C C + C C C C + C C C C

C C C
C C C C C C C C C C C C
f our double bonds
-Farnesene -Farnesene
 -Farnesene

O O
O
O 3/Zn/H 2 O O CH 2 + +
+ +
H 2C O
O
O
O

-Farnesene
O
O
CH 2
O
O
O O
O
O
H 2C

[O]
O
O

HOOC
O

O
[O] COOH
O COOH
O
 -Farnesene -Farnesene

i) PCl5/lutidine CH2O
ii) NaNH2/liq NH3 C C
O
CNa C

CH 2OH

i) LiAlH4/AlCl3
ii) I2

Me2CuLi
CH2OH CH2OH
I
CH2 OH

CrO3
CH2 OH CHO

3H2
CH2 OH CH2 OH
 O
O O
O3 /Zn/H 2O
O CH2 OH O +
O
O CH2 OH + 2

O H
O O