4.8 Article

Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 40, Pages 12770-12774

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b09965

Keywords

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Funding

  1. National Institutes of Health [R01GM121678]
  2. University of California Irvine
  3. Hellman Foundation
  4. National Science Foundation [DGE-1321846]
  5. Natural Sciences and Engineering Research Council of Canada [PGSD3-487506-2016]
  6. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM121678] Funding Source: NIH RePORTER

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A short, enantioselective synthesis of (-)-nodulisporic acid C is described. The route features two highly diastereoselective polycyclizations en route to the terpenoid core and the indenopyran fragment and a highly convergent assembly of a challenging indole moiety. Application of this chemistry allows for a 12-step synthesis of the target indoloterpenoid from commercially available material.

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