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Synthesis of (+)‐Discodermolide by Catalytic Stereoselective Borylation Reactions
Author(s) -
Yu Zhiyong,
Ely Robert J.,
Morken James P.
Publication year - 2014
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.201405455
Subject(s) - borylation , hydroboration , chemistry , stereoselectivity , natural product , alkylation , diene , combinatorial chemistry , aldehyde , stereochemistry , aldol reaction , catalysis , enantioselective synthesis , total synthesis , organic chemistry , alkyl , aryl , natural rubber
The marine natural product (+)‐discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4‐diboration of dienes and borylative diene–aldehyde couplings in complex‐molecule synthesis.