Diastereodivergent total synthesis of mosquito oviposition pheromone-Reference-Cited by-同舟云学术

Diastereodivergent total synthesis of mosquito oviposition pheromone

Published:2014 Issue:30 Volume:4 Page:15552-15557
ISSN:2046-2069
Container-title:RSC Adv.
language:en
Short-container-title:RSC Adv.

Author:

Hurem David¹²³,Dudding Travis¹²³

Affiliation:

1. Department of Chemistry

2. Brock University

3. St. Catharines, Canada

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.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2014/RA/C4RA01542H

Reference44 articles.

1. The Influence of the Apical Droplet of Culex Egg Rafts on Oviposition of Culex Pipiens Faticans (Diptera: Culicidae)

2. erythro-6-Acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone

3. Synthesis of both the enantiomers of erythro-6-acetoxy-5-hexadecanolide

4. Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide

5. Attractancy and species specificity of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone

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