4.8 Article

The Taumycin A Macrocycle: Asymmetric Total Synthesis and Revision of Relative Stereochemistry

Journal

ORGANIC LETTERS
Volume 16, Issue 19, Pages 5196-5199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5025585

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Funding

  1. National Institutes of Health [SC2-GM099595-02]
  2. NIH Maximizing Access to Research Careers (MARC) program [NTH GM07667-36]

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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 alpha-keto ketene macrocylization 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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