Cytochalasans are a prominent family of fungal metabolites with over 500 members having been identified so far. Recently, the chemical diversity of cytochalasans has been significantly enriched with the continuous discovery of a series of unprecedented merocytochalasans. These newly discovered merocytochalasans pose daunting challenges to total synthesis. Fascinated by their structure, we initiated a program towards their total synthesis. Our synthetic strategy largely based on the proposed biosynthetic pathway, we first developed a concise synthetic route towards the monomeric aspochalasin B, then an intermolecular Diels-Alder reaction were employed to achieve the dimeric asperchalasins B-E, finally the formal [5+2] reaction was realized to access the trimeric asperchalasin A and asperflavipine B. We have achieved the collective synthesis of an array of tricyclic, heterodimeric and heterotrimeric cytochalasins, which largely enriches the synthetic chemistry of cytochalasins.

Biomimetic total syntheses of asperchalasines A-E and asperflavipine B

ACS Spring 2022

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