Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm

A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthe...

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Detalles Bibliográficos
Autores principales: Sun, Zhi-Feng, Zhang, Tao, Liu, Jinyang, Du, Zhen-Ting, Zheng, Huaiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017750/
https://www.ncbi.nlm.nih.gov/pubmed/29543774
http://dx.doi.org/10.3390/molecules23030667
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author Sun, Zhi-Feng
Zhang, Tao
Liu, Jinyang
Du, Zhen-Ting
Zheng, Huaiji
author_facet Sun, Zhi-Feng
Zhang, Tao
Liu, Jinyang
Du, Zhen-Ting
Zheng, Huaiji
author_sort Sun, Zhi-Feng
collection PubMed
description A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.
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spelling pubmed-60177502018-11-13 Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm Sun, Zhi-Feng Zhang, Tao Liu, Jinyang Du, Zhen-Ting Zheng, Huaiji Molecules Communication A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone. MDPI 2018-03-15 /pmc/articles/PMC6017750/ /pubmed/29543774 http://dx.doi.org/10.3390/molecules23030667 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Sun, Zhi-Feng
Zhang, Tao
Liu, Jinyang
Du, Zhen-Ting
Zheng, Huaiji
Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title_full Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title_fullStr Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title_full_unstemmed Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title_short Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
title_sort asymmetric total synthesis of four stereoisomers of the sex pheromone of the western corn rootworm
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017750/
https://www.ncbi.nlm.nih.gov/pubmed/29543774
http://dx.doi.org/10.3390/molecules23030667
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