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Total Synthesis of Asperchalasines A, D, E, and H
Author(s) -
Long Xianwen,
Ding Yiming,
Deng Jun
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808481
Subject(s) - chemistry , intermolecular force , cycloaddition , stereoselectivity , monomer , total synthesis , stereochemistry , combinatorial chemistry , molecule , organic chemistry , catalysis , polymer
The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular Diels–Alder reaction followed by a biomimetic oxidative heterodimerization by 5+2 cycloaddition to furnish asperchalasine A. The synthetic efforts provide insight into the biosynthetic pathway of cytochalasan dimers and enables the further study of their biological properties.