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Synlett 2020; 31(04): 301-308
DOI: 10.1055/s-0039-1691500
DOI: 10.1055/s-0039-1691500
synpacts
Total Synthesis of Asperchalasine A
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.Weitere Informationen
Publikationsverlauf
Received: 19. Oktober 2019
Accepted after revision: 11. November 2019
Publikationsdatum:
13. Dezember 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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For isolation of merocytochalasans, see:
For isolation of aspochalasin B, see:
For recent syntheses of aspochalasin B, see:
Acid-promoted isobenzofuran formation:
Base-promoted isobenzofuran formation: