Diastereodivergent total synthesis of mosquito oviposition pheromone?

RSC Advances Pub Date: 2014-03-17 DOI: 10.1039/C4RA01542H

Abstract

The unnatural threo-6-acetoxy-5-hexadecanolide and the natural mosquito oviposition pheromone erythro-6-acetoxy-5-hexadecanolide were synthesized in a diastereodivergent fashion in 44% and 33% overall yield respectively from 5-bromovaleric acid and undecanal. The key step utilized a chemoenzymatic epoxidation-lactonization of a naturally available fatty acid to form the 6-hydroxy-5-hexadecanolide core.

Graphical abstract: Diastereodivergent total synthesis of mosquito oviposition pheromone
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