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Total Synthesis and Stereochemical Reassignment of (+)‐Neopeltolide
Author(s) -
Youngsaye Willmen,
Lowe Jason T.,
Pohlki Frauke,
Ralifo Paul,
Panek James S.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704122
Subject(s) - stereocenter , enantioselective synthesis , total synthesis , computer science , annulation , oxazole , construct (python library) , stereochemistry , chemistry , programming language , organic chemistry , catalysis
Take a closer look! The first enantioselective total synthesis, stereochemical reassignment, and absolute configuration of the metabolite neopeltolide is described (see picture). Synthetic highlights of this route include a modified Evans–Tishchenko reduction to introduce the C11 stereocenter, [4+2] annulation to construct the pyran system, and a Still–Gennari olefination to install the oxazole side chain.