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手性接触性信息素及其对映体的不对称合成。

Asymmetric Synthesis of Contact Sex Pheromone of and Its Enantiomer.

机构信息

Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, China.

College of Enviromental Sciences, Sichuan Agricultural University, 211 Huimin Road, Chengdu 611130, China.

出版信息

Molecules. 2022 Oct 14;27(20):6897. doi: 10.3390/molecules27206897.

DOI:10.3390/molecules27206897
PMID:36296492
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9611917/
Abstract

is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, ()-11-methyl-heptacosane, and its enantiomer were synthesized via Evans' chiral auxiliaries. The key steps of this approach included acylation of carboxylic acid, diastereoselective methylation of oxazolidinone amide, and Wittig coupling of the aldehyde with chiral phosphonium salt. The synthetic pheromones would have potential utility in the control of this pest.

摘要

是一种有害的森林害虫,它会攻击云杉。该害虫的接触性性信息素()-11-甲基二十七烷和其对映异构体通过 Evans 手性助剂合成。该方法的关键步骤包括羧酸的酰化、恶唑烷酮酰胺的立体选择性甲基化以及醛与手性膦盐的Wittig 偶联。这些合成的信息素在控制这种害虫方面可能具有潜在的应用价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/ac18a2f6b919/molecules-27-06897-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/519e44b37e3b/molecules-27-06897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/b072c5ee767b/molecules-27-06897-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/82d0574d3b24/molecules-27-06897-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/606a0dd47e06/molecules-27-06897-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/ac18a2f6b919/molecules-27-06897-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/519e44b37e3b/molecules-27-06897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/b072c5ee767b/molecules-27-06897-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/82d0574d3b24/molecules-27-06897-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/606a0dd47e06/molecules-27-06897-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ee3/9611917/ac18a2f6b919/molecules-27-06897-sch004.jpg

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