Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium‐Catalyzed Allylic Etherification: Total Synthesis of Gaur Acid | Zendy

Evans P. Andrew | Zendy; Leahy David K. | Zendy; Andrews William J. | Zendy; Uraguchi Daisuke | Zendy

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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.

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