Palladium‐Catalyzed DYKAT of Vinyl Epoxides: Enantioselective Total Synthesis and Assignment of the Configuration of (+)‐Broussonetine G | Zendy

Trost Barry M. | Zendy; Horne Daniel B. | Zendy; Woltering Michael J. | Zendy

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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.

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