Organic SYNTHESIS

WEEK 1

By
Dr RAJA SHAHID ASHRAF
Department of Chemistry
GCU, Lahore
What we will learn in this course?

How to design new molecules or synthesize known

naturally occurring materials?

Two approaches widely used:

Random and retrosynthesis
 Retrosynthesis : thinking backwards
from relatively complex molecules to
simpler ones using the disconnection
approach.

Course Book
 Retrosynthesis – First Report
Robert Robinson was the first scientist to suggest the idea by
publishing his famous Tropinone Synthesis in 1917. He used the term
“imaginary hydrolysis” and put dash lines to show disconnection.

Improved Synthesis in 1935

 Tropinone Synthesis - Mechanism
double Mannich reaction tandem reaction in a one-pot synthesis
The Mannich reaction is an analogue of the aldol reaction that
uses an iminium ion electrophile instead of a ketone or
aldehyde

acetonedicarboxylic acid is known as the "synthetic equivalent

1,3-dicarboxylic acid groups are called "activating groups" to facilitate the ring formation
A well known way to make acetal
The disconnection:
The disconnection:
The disconnection:

Multistriatin
Warren’s Organic Synthesis, the disconnection approach Chapter 1