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Total Synthesis of Mycalolides A and B through Olefin Metathesis
Author(s) -
Kita Masaki,
Oka Hirotaka,
Usui Akihiro,
Ishitsuka Tomoya,
Mogi Yuzo,
Watanabe Hidekazu,
Tsunoda Masaki,
Kigoshi Hideo
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507795
Subject(s) - olefin metathesis , total synthesis , metathesis , olefin fiber , chemistry , side chain , salt metathesis reaction , enantioselective synthesis , acyclic diene metathesis , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymerization , polymer
An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps.