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基于烯二醇盐的Tsuji-Trost反应全合成解剖醇A。

Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction.

作者信息

Andringa Ruben L H, Marinus Nittert, Bunt Daan V, Haiderer Elizabeth R, Abramovitch Robert B, Brown Christopher D, Rhee Kyu Y, Witte Martin D, Minnaard Adriaan J

机构信息

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

Department of Microbiology, Genetics and Immunology, Michigan State University East Lansing MI 48824 USA.

出版信息

Chem Sci. 2024 Jun 7;15(27):10541-10546. doi: 10.1039/d4sc01745e. eCollection 2024 Jul 10.

DOI:10.1039/d4sc01745e
PMID:38994423
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11234881/
Abstract

Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell and does not inhibit growth of the bacterium.

摘要

Dissectol A是一种从多种开花植物中分离出的重排萜烯糖苷。以葡萄糖为起始原料,通过位点选择性氧化以及以烯二醇盐为亲核试剂的分子内烯丙基烷基化反应,制备出了这种官能团密集的双环结构。尽管有早期报道,但Dissectol A在全细胞中对DevRS信号传导并无抑制作用,也不抑制该细菌的生长。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5899/11234881/20ec8dc629ac/d4sc01745e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5899/11234881/20ec8dc629ac/d4sc01745e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5899/11234881/20ec8dc629ac/d4sc01745e-s2.jpg

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