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Total Synthesis of (+)‐Isomigrastatin
Author(s) -
Krauss Isaac J.,
Mandal Mihirbaran,
Danishefsky Samuel J.
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.200701837
Subject(s) - isomerization , context (archaeology) , phosphine , natural product , total synthesis , chemistry , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , biology , paleontology
Marginally stable natural products : The asymmetric total synthesis of the hydrolytically and thermally labile natural product (+)‐isomigrastatin was demonstrated. The thermodynamic instability of a 2 E ‐configured double bond in the context of this 12‐membered macrolide was further demonstrated by phosphine‐catalyzed isomerization to the 2 Z configuration.