4.8 Article

Total Synthesis of (-)-N-Methylwelwitindolinone C Isothiocyanate

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 40, Pages 15797-15799

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja206538k

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Funding

  1. NIH-NIGMS [R01 GM090007]
  2. Boehringer Ingelheim
  3. DuPont
  4. Eli Lilly
  5. Amgen
  6. University of California, Los Angeles
  7. ACS Organic Division
  8. Bristol-Myers Squibb
  9. Foote Family

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We report the first total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.

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