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

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

Saibal Das, Anand Kumar Mishra, Ashish Kumar, Ahamad Al Khazim Al Ghamdi and Jhillu Singh Yadav
Carbohydrate research, Vol.358, pp.7-11
01/09/2012
DOI: https://doi.org/10.1016/j.carres.2012.05.009
PMID: 22687338

Abstract

Biochemistry & Molecular Biology Chemistry Chemistry, Applied Chemistry, Organic Life Sciences & Biomedicine Physical Sciences Science & Technology
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 d-gluconolactone in 18% overall yield making it simple, practical and elegant. (C) 2012 Elsevier Ltd. All rights reserved.

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