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Palladium‐Catalyzed DYKAT of Vinyl Epoxides: Enantioselective Total Synthesis and Assignment of the Configuration of (+)‐Broussonetine G
Author(s) -
Trost Barry M.,
Horne Daniel B.,
Woltering Michael J.
Publication year - 2003
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.200352857
Subject(s) - enantioselective synthesis , palladium , pyrrolidine , chemistry , catalysis , nucleophile , total synthesis , allylic rearrangement , stereochemistry , epoxide , combinatorial chemistry , organic chemistry
A potential general approach to potent N‐heterocyclic glycosidase inhibitors is illustrated by the first total synthesis of (+)‐broussonetine G ( 1 ). The key transformation of the synthesis relies on two successive palladium‐catalyzed asymmetric allylic alkylations of butadiene monoxide with a nitrogen nucleophile to construct the pyrrolidine core.