A Concise Synthesis of Eupomatilones 4, 6, and 7 by Rhodium‐Catalyzed Enantioselective Desymmetrization of Cyclic  meso  Anhydrides with Organozinc Reagents Generated In Situ | Zendy

Johnson Jeffrey B. | Zendy; Bercot Eric A. | Zendy; Williams Catherine M. | Zendy; Rovis Tomislav | Zendy

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A Concise Synthesis of Eupomatilones 4, 6, and 7 by Rhodium‐Catalyzed Enantioselective Desymmetrization of Cyclic meso Anhydrides with Organozinc Reagents Generated In Situ

Author(s) -

Johnson Jeffrey B.,

Bercot Eric A.,

Williams Catherine M.,

Rovis Tomislav

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.200700816

Subject(s) - desymmetrization , enantioselective synthesis , rhodium , chemistry , nucleophile , catalysis , phosphoramidite , in situ , reagent , organic chemistry , yield (engineering) , combinatorial chemistry , stereochemistry , materials science , biochemistry , dna , oligonucleotide , metallurgy

The wages of syn : The development of a phosphoramidite‐ligated rhodium catalyst allows the enantioselective desymmetrization of cyclic anhydrides with organozinc nucleophiles formed in situ. This methodology has been utilized for a concise synthesis of eupomatilones 4 and 7 and of the putative structure of eupomatilone 6, each of which is completed in four steps in greater than 50 % overall yield.

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