Question

How would you synthesize racemic disparlure (Problem 18-63) from compounds having ten or fewer carbons?

Short answer

The answer is

Step-by-step solution

Step-by-step Solution

The Disparlure, is a sex attractant released by the female gypsy moth called Lymantria dispar.

Reaction of disparlure with acid and then with potassium permanganate yields two carboxylic acids gives undecanoic acid and 6-methyl- heptanoic acid.

Explanation

The reaction for the synthesis of racemic Displature is shown below.

The compound can be synthesized starting from the 7-methyl octane. It is oxidised using sodium hydrazine, followed by nucleophilic substitution reaction with bromodecane. The triple bond is reduced to cis- alkene using the Lindlars catalyst. The obtained alkene on epoxidation with peroxide gives the racemic mixture of Displature.