4.8 Article

Total Synthesis of Kingianin A

Journal

ORGANIC LETTERS
Volume 15, Issue 2, Pages 398-401

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol303388k

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Funding

  1. National Institutes of Health [GM 74776]
  2. Stony Brook University

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A 12-step synthesis of kingianin A, an inhibitor of the antiapoptotic protein Bcl-xL, Is based on a radical cation Diels-Alder reaction (RCDA). This approach is thought to be biomimetic. The use of a tether in the key RCDA step controls the regiochemistry of the cycloaddition, leading to the desired core structure and a separable diastereomer.

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