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茶毛虫雌蛾性信息素的非对映体全合成。

The Asymmetric Total Synthesis of the Female-Produced Sex Pheromone of the Tea Tussock Moth.

机构信息

Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China.

出版信息

Molecules. 2024 Aug 15;29(16):3866. doi: 10.3390/molecules29163866.

DOI:10.3390/molecules29163866
PMID:39202945
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11357487/
Abstract

The tea tussock moth is a pest that damages tea leaves, affecting the quality and yield of tea and causing huge economic losses. The efficient asymmetric total synthesis of the sex pheromone of the tea tussock moth was achieved using commercially available starting materials with a 25% overall yield in 11 steps. Moreover, the chiral moiety was introduced by Evans' template and the key C-C bond construction was accomplished through Julia-Kocienski olefination coupling. The synthetic sex pheromone of the tea tussock moth will facilitate the subsequent assessment and implementation of pheromones as environmentally friendly tools for pest management.

摘要

茶蓑蛾是一种危害茶叶的害虫,会影响茶叶的质量和产量,造成巨大的经济损失。本文使用商业可得的起始原料,通过 11 步反应以 25%的总收率,高效不对称全合成了茶蓑蛾性信息素,其中手性中心通过 Evans 诱导的方法引入,关键 C-C 键的构建则通过 Julia-Kocienski 烯烃化偶联反应完成。茶蓑蛾性信息素的合成将有助于后续评估和实施信息素作为害虫管理的环保工具。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/034c34c4c687/molecules-29-03866-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/4f25bb544ec1/molecules-29-03866-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/7fe6196de188/molecules-29-03866-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/59d6e38095e3/molecules-29-03866-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/cdba7c1e5e45/molecules-29-03866-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/034c34c4c687/molecules-29-03866-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/4f25bb544ec1/molecules-29-03866-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/7fe6196de188/molecules-29-03866-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/59d6e38095e3/molecules-29-03866-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/cdba7c1e5e45/molecules-29-03866-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7389/11357487/034c34c4c687/molecules-29-03866-sch004.jpg

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J Insect Sci. 2021 Jul 1;21(4). doi: 10.1093/jisesa/ieab045.
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