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Total Syntheses of Asperchalasines A–E
Author(s) -
Bao Ruiyang,
Tian Chong,
Zhang Haoyu,
Wang Zhiguo,
Dong Zhen,
Li Yuanhe,
Gao Mohan,
Zhang Haolin,
Liu Gang,
Tang Yefeng
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808249
Subject(s) - cycloaddition , chemistry , monomer , diels–alder reaction , ring closing metathesis , salt metathesis reaction , total synthesis , stereochemistry , metathesis , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
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.