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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.