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Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium‐Catalyzed Allylic Etherification: Total Synthesis of Gaur Acid
Author(s) -
Evans P. Andrew,
Leahy David K.,
Andrews William J.,
Uraguchi Daisuke
Publication year - 2004
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.200460612
Subject(s) - regioselectivity , allylic rearrangement , rhodium , total synthesis , catalysis , chemistry , organic chemistry , stereochemistry
A dramatic enhancement of the stereospecificity of the title reaction was observed with trimethylphosphite‐modified copper( I ) alkoxide reagents. The combination of this reaction with ring‐closing metathesis provides a direct approach to cis ‐ and trans ‐disubstituted cyclic ethers (see scheme). A seven‐step total synthesis of the natural product gaur acid highlighted the potential of this methodology. LG=leaving group.