Decarboxylative Grob‐Type Fragmentations in the Synthesis of Trisubstituted  Z  Olefins: Application to Peloruside A, Discodermolide, and Epothilone D | Zendy

Prantz Kathrin | Zendy; Mulzer Johann | Zendy

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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.

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