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An Enantioselective Total Synthesis of (+)‐Peloruside A
Author(s) -
McGowan Meredeth A.,
Stevenson Christian P.,
Schiffler Matthew A.,
Jacobsen Eric N.
Publication year - 2010
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.201002177
Subject(s) - stereocenter , enantioselective synthesis , catalysis , ring (chemistry) , total synthesis , chemistry , sequence (biology) , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
Short and sweet : Chiral epoxides, prepared using (salen)cobalt‐catalyzed ring‐opening reactions, and a chromium catalyst controlled hetero‐Diels–Alder reaction were used to set most of the stereocenters in the total synthesis of the microtubule‐stabilizing agent peloruside A. The overall highly convergent route required only 20 steps in the longest linear sequence. MOM=methoxymethyl, TBS= tert ‐butyldimethylsilyl.