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Issue 30, 2014
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Diastereodivergent total synthesis of mosquito oviposition pheromone

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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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Supplementary files

Article information


Submitted
21 Feb 2014
Accepted
17 Mar 2014
First published
17 Mar 2014

RSC Adv., 2014,4, 15552-15557
Article type
Paper
Author version available

Diastereodivergent total synthesis of mosquito oviposition pheromone

D. Hurem and T. Dudding, RSC Adv., 2014, 4, 15552
DOI: 10.1039/C4RA01542H

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