A Convenient Synthesis of Four Stereoisomers of 6-Acetoxy-5-hexadecanolide, the Major Component of the Mosquito Oviposition Attractant Pheromone

Abstract

The major component of the mosquito oviposition attractant pheromone (5S,6R)-(+)- and (5R, 6S)-(–)-erythro-6-acetoxy-5-hexadecanolide and their threo-isomers, (5R, 6R)-(+)- and (5S,6S)-(–)-6-acetoxy-5-hexadecanolide were synthesized from isopropylidene-d-glyceraldehyde and isopropylidene-L-glyceraldehyde, respectively, in which the nucleophilic addition of Grignard reagent involved the diastereoface-differentiating process as the key step.

The bioassay of four erythro- and threo-isomers against mosquito (Culex pipiens molestus) was conducted. (5R, 6S)-(–)-erythro-6-acetoxy-5-hexadecanolide proved to be the most effective as an attractant.