Organic Synthesis

Retrosynthesis
Synthetic planning starts with the product, which is fixed and
unchangeable, and works backwards towards the starting materials. This
process is called retrosynthesis, and the art of planning the synthesis of a
target molecule is called retrosynthetic analysis.

Synthetic design involves two distinct steps:

(1) retrosynthetic analysis and
(2) subsequent translation of the analysis into a "forward direction" synthesis.
Using Arrows in Equations and Reaction Mechanisms
Common Acceptor Synthons
Synthon Synthetic equivalent
 Common Donor Synthons

Synthetic
Synthon Derived reagent equivalent
Retrosynthetic anaylsis A

Synthesis A
Retrosynthetic anaylsis B

Synthesis B
 One Functional Group Analysis

Synthesis (path a)
 Two Functional Groups in a 1,3-Relationship
Analysis

Synthesis (path a)

Presence of a -hydroxy
ketone moiety in the TM
suggest a retroaldol transform.
 Analysis

However, path b is preferable since it

does not require a selective functional
group interconversion (reduction).

Synthesis (path b)
 Two Functional Groups in a 1,4-Relationship
Analysis

2,5-hexanedione

Synthesis

The -carbon in this synthon

requires an inversion of polarity.
(-bromo ketone)
 Analysis

5-hydroxy-2-hexanone

Synthesis

Inversion of the polarity in the

acceptor synthon is accomplished
by using the electrophilic epoxide
as the corresponding SE.