Asymmetric Total Synthesis of (−)-Spirochensilide A, Part 1: Diastereoselective Synthesis of the ABCD Ring and Stereoselective Total Synthesis of 13(R)‑Demethyl Spirochensilide A

A concise and diastereoselective construction of the ABCD ring system of spirochensilide A is described. The key steps of this synthesis are a semipinacol rearrangement reaction to stereoselectively construct the AB ring system bearing two vicinal quaternary chiral centers and a Co-mediated Pauson–K...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2135-2157
Main Authors: Liang, Xin-Ting, Sun, Bao-Chuan, Liu, Chang, Li, Yuan-He, Zhang, Nan, Xu, Qian-Qian, Zhang, Zhong-Chao, Han, Yi-Xin, Chen, Jia-Hua, Yang, Zhen
Format: Article
Language:English
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Summary:A concise and diastereoselective construction of the ABCD ring system of spirochensilide A is described. The key steps of this synthesis are a semipinacol rearrangement reaction to stereoselectively construct the AB ring system bearing two vicinal quaternary chiral centers and a Co-mediated Pauson–Khand reaction to form the spiro-based bicyclic CD ring system. This chemistry leads to the stereoselective synthesis of 13­(R)-demethyl spirochensilide A, paving the way for the first asymmetric total synthesis of (−)-spirochensilide A.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02494