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(R)-松茸醇及其风味类似物的通用不对称合成

A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

作者信息

Liu Jia, Li Honglian, Zheng Chao, Lu Shichao, Guo Xianru, Yin Xinming, Na Risong, Yu Bin, Wang Min

机构信息

Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou 450002, China.

Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 57115, China.

出版信息

Molecules. 2017 Feb 27;22(3):364. doi: 10.3390/molecules22030364.

DOI:10.3390/molecules22030364
PMID:28264452
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6155351/
Abstract

An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. ()-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. These chiral allyl alcohols are prepared for food analysis and screening insect attractants.

摘要

通过末端炔烃对醛的不对称加成,开发了一种高效实用的合成手性松茸醇及其类似物的路线。()-松茸醇和其他风味物质可由各种烷基醛以高产率(三步反应中高达49.5%)和优异的对映体过量(高达>99%)顺利合成。该方法可作为天然脂肪酸代谢物和类似物活性小分子文库的一种替代不对称合成方法。这些手性烯丙醇可用于食品分析和筛选昆虫引诱剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/9524f6e57de0/molecules-22-00364-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/e3976d0862dc/molecules-22-00364-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/e937d4b86596/molecules-22-00364-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/3d52facc9f0a/molecules-22-00364-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/42fb13643e26/molecules-22-00364-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/9524f6e57de0/molecules-22-00364-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/e3976d0862dc/molecules-22-00364-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/e937d4b86596/molecules-22-00364-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/3d52facc9f0a/molecules-22-00364-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/42fb13643e26/molecules-22-00364-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf7d/6155351/9524f6e57de0/molecules-22-00364-sch004.jpg

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