Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

Abstract

2,3-Butanediacetal derivatives were used for the stereoselective synthesis of unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material.

Keywords

• 2,3-butanediacetal
• cis-epoxide
• (−)-disparlure
• (+)-disparlure
• (−)-monachalure
• (+)-monachalure