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一种无保护基团的马铃薯甲虫信息素的合成方法。

A protecting group-free synthesis of the Colorado potato beetle pheromone.

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.

出版信息

Beilstein J Org Chem. 2013 Nov 6;9:2374-7. doi: 10.3762/bjoc.9.273. eCollection 2013.

DOI:10.3762/bjoc.9.273
PMID:24367402
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3869274/
Abstract

A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.

摘要

一种新型的聚集信息素合成方法，用于开发科罗拉多马铃薯甲虫（Leptinotarsa decemlineata），该方法基于 Sharpless 不对称环氧化反应与使用催化 [(neocuproine)PdOAc]2OTf2 的化学选择性醇氧化反应相结合。采用这种方法，从香叶醇出发，经过 3 步反应，以 80%的产率和 86%的对映选择性合成了信息素，总收率为 80%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/978794c8d06b/Beilstein_J_Org_Chem-09-2374-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/024f37838577/Beilstein_J_Org_Chem-09-2374-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/0b244fab521b/Beilstein_J_Org_Chem-09-2374-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/550e36fc0d8e/Beilstein_J_Org_Chem-09-2374-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/b206acbabd91/Beilstein_J_Org_Chem-09-2374-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/978794c8d06b/Beilstein_J_Org_Chem-09-2374-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/024f37838577/Beilstein_J_Org_Chem-09-2374-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/0b244fab521b/Beilstein_J_Org_Chem-09-2374-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/550e36fc0d8e/Beilstein_J_Org_Chem-09-2374-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/b206acbabd91/Beilstein_J_Org_Chem-09-2374-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc60/3869274/978794c8d06b/Beilstein_J_Org_Chem-09-2374-g006.jpg

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