Synlett 2020; 31(04): 301-308
DOI: 10.1055/s-0039-1691500
synpacts
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Asperchalasine A

Xianwen Long
a  State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, P. R. of China   Email: [email protected]
b  University of Chinese Academy of Sciences, Beijing 100049   P. R. of China
,
Yiming Ding
a  State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, P. R. of China   Email: [email protected]
b  University of Chinese Academy of Sciences, Beijing 100049   P. R. of China
,
Hai Wu
a  State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, P. R. of China   Email: [email protected]
b  University of Chinese Academy of Sciences, Beijing 100049   P. R. of China
,
Jun Deng
a  State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, P. R. of China   Email: [email protected]
› Author Affiliations
Financial support from the National Natural Science Foundaion of China (Grant No. 21871278), the Chinese Academy of Sciences, Pioneer Hundred Talents Program (Grant No. 2017-022), and the Start-up funding of Kunming Institute of Botany is gratefully acknowledged.
Further Information

Publication History

Received: 19 October 2019

Accepted after revision: 11 November 2019

Publication Date:
13 December 2019 (online)


Abstract

Here we briefly reviewed recent synthetic progress toward cytochalasan trimer, asperchalasine A by Tang, Trauner and our group. This process features a highly stereoselective intermolecular Diels–Alder reaction and a HWE or RCM macrocyclization to establish the key monomer aspochalasin B. A late-stage biomimetic oxidative dearomatization of triphenol and subsequent [5+2] cycloaddition cascade furnished asperchalasine A. We anticipate that this key reaction could also be used for the synthesis of other merocytochalasans, and provide some insight into the biosynthetic connections of merocytochalasans.
1 Introduction
2 Total Synthesis of Aspochalasin B
3 Total Synthesis of Asperchalasine A
4 Conclusions

 
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