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The Taumycin A Macrocycle: Asymmetric Total Synthesis and Revision of Relative Stereochemistry
Author(s) -
Justine N. deGruyter,
William A. Maio
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5025585
Subject(s) - chemistry , ketene , diastereomer , total synthesis , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
The first asymmetric total synthesis and revision of the relative configuration of the 12-membered taumycin A macrocycle is described. Key to the success of this work was a novel α-keto ketene macrocyclization that provided an efficient means by which to access two diastereomers of the desired macrolide without the need to employ additional coupling agents or unnecessary oxidation state adjustments.

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