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Decarboxylative Grob‐Type Fragmentations in the Synthesis of Trisubstituted Z Olefins: Application to Peloruside A, Discodermolide, and Epothilone D
Author(s) -
Prantz Kathrin,
Mulzer Johann
Publication year - 2009
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.200901740
Subject(s) - chemistry , stereochemistry , aldol reaction , epothilone , fragmentation (computing) , enantioselective synthesis , stereoselectivity , organic chemistry , catalysis , computer science , programming language
Discriminating elimination : A new method for the synthesis of methyl‐branched trisubstituted Z olefins, a structural motif in many polyketides with anticancer activity, relies on an − OH‐induced decarboxylative Grob‐type fragmentation (see scheme; Ms=mesyl). The starting materials are β‐mesyloxy lactones with a quaternary α center, which are prepared by aldol reactions in a diastereo‐ and enantioselective manner.