Total Synthesis of Asperchalasine A

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

Key words

biomimetic synthesis - [5+2] cycloaddition - natural products - total synthesis - dimerization

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