Issue 40, 2015
From the journal:

Chemical Communications

Total synthesis of (−)-exiguolide via an organosilane-based strategy†

Hongze Li,a   Hengmu Xie,a   Zhigao Zhang,a   Yongjin Xu,a   Ji Lu,a   Lu Gaoa  and  Zhenlei Song*ab  

* Corresponding authors

a Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
E-mail: zhenleisong@scu.edu.cn

b State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, China

Abstract

An organosilane-based strategy has been used to accomplish the convergent total synthesis of (−)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the 20-membered macrocycle; and (3) Hiyama–Denmark cross-coupling of vinylsilane with vinyliodide to install the triene side chain.

Graphical abstract: Total synthesis of (−)-exiguolide via an organosilane-based strategy

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Article information

DOI
https://doi.org/10.1039/C5CC02448J
Article type
Communication
Submitted
24 Mar 2015
Accepted
10 Apr 2015
First published
10 Apr 2015

Chem. Commun., 2015,51, 8484-8487

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Total synthesis of (−)-exiguolide via an organosilane-based strategy

H. Li, H. Xie, Z. Zhang, Y. Xu, J. Lu, L. Gao and Z. Song, Chem. Commun., 2015, 51, 8484 DOI: 10.1039/C5CC02448J

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