Facile total synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant pheromone

Abstract

Total synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide, a major component of mosquito oviposition attractant pheromones is reported. The key synthetic steps involve epoxide opening by lithiated salt of ethylpropionate and acid catalysed lactonization. The total synthesis was achieved in 11 linear steps staring from a readily available carbohydrate δ-gluconolactone in 18% overall yield making it simple, practical and elegant. © 2012 Elsevier Ltd. All rights reserved.