asperchalasines A-E 的全合成。
Total Syntheses of Asperchalasines A-E.
机构信息
School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Tsinghua University, Beijing, 100084, China.
Beijing National Laboratory for Molecular Sciences (BNLMS), College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
出版信息
Angew Chem Int Ed Engl. 2018 Oct 22;57(43):14216-14220. doi: 10.1002/anie.201808249. Epub 2018 Oct 4.
The first total syntheses of asperchalasines A-E, a collection of unprecedented merocytochalasans, are reported. Aspochalasin B, a key tricyclic cytochalasan monomer, was first synthesized through a unified approach that hinges on a Diels-Alder reaction and a ring-closing metathesis reaction. The bioinspired Diels-Alder reactions of aspochalasin B with different epicoccine precursors were then explored, which enabled the divergent access of the heterodimers asperchalasines B-E as well as related congeners. Furthermore, the heterotrimer asperchalasine A was obtained from one epicoccine unit and two aspochalasin B units through a biomimetic Diels-Alder reaction followed by an oxidative [5+2]-cycloaddition.
首次全合成了asperchalasines A-E，这是一组前所未有的 merocytochalasans。其中，asperchalasin B 是关键的三环细胞松弛素单体，首次通过统一的方法合成，该方法依赖于 Diels-Alder 反应和环 closing metathesis 反应。然后探索了生物启发的 Diels-Alder 反应，asperchalasin B 与不同的 epicoccine 前体反应，从而实现了 heterodimers asperchalasines B-E 以及相关同系物的发散式合成。此外，通过仿生 Diels-Alder 反应和随后的氧化 [5+2]-环加成，从一个 epicoccine 单元和两个 aspochalasin B 单元获得了 heterotrimer asperchalasine A。
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