Advices For Studying Organic Chemistry

CONJUGATED UNSATURATED SYSTEMS

MOLECULES WITH THE NOBEL PRIZE IN

THEIR SYNTHETIC LINEAGE (ANCESTRY)

1. The Diels-Alder reaction:
   
   
   1. Otto Diels and Kurt Alder won the Nobel Prize for Chemistry in 1950 for
      developing this reaction.
   
   
   2. It can form a six-membered ring with as many as four new stereocenters created
      in a single stereospecific step from acyclic precursors.
   
   
   3. It also produces a double bond that can be used to introduce other functionality.
   
   
   
   


2. Molecules that have been synthesized using Diels-Alder reaction include:

HO

HO

N

H CH 3

H

Morphine

N N

H

MeO

H

H

MeO 2 C

H

OMe

OO

MeO

OMe

OMe

Reserpine

H

O

O

CH 3

H

H

H

CH 3

OH

O

CH 2 OH

Cortisone

CH 3

O

CH 3 H

H

OH

O

O CH 2 OH

1) Morphine (M. Gates): the hypnotic sedative used after many surgical procedures.

2) Reserpine (R. B. Woodward): a clinically used antipypertensive agent.

3) Chlesterol (R. B. Woodward): precursor of all steroids in the body.