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The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.

ABSTRACT: 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 ?-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.

SUBMITTER: deGruyter JN 

PROVIDER: S-EPMC4184443 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.

deGruyter Justine N JN   Maio William A WA  

Organic letters 20140923 19

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. ...[more]

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