4.8 Article

Synthesis and Structure Revision of Nakiterpiosin

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 4, Pages 1410-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja808110d

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Funding

  1. NIH [R01-GM079554]
  2. Welch Foundation [I-1596]
  3. UT Southwestern
  4. Southwestern Medical Foundation Scholar

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This manuscript describes a convergent synthesis and the revision of the relative stereochemistry of nakiterpiosin, a marine C-nor-D-homosteroid. Our synthesis features a late-stage carbonylative Stille cross-coupling reaction and a photo-Nazarov cyclization reaction that deliver the complete nakiterpiosin skeleton efficiently.

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