4.8 Article

Approaches to N-Methylwelwitindolinone C Isothiocyanate: Facile Synthesis of the Tetracyclic Core

Journal

ORGANIC LETTERS
Volume 12, Issue 11, Pages 2492-2495

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1006373

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Funding

  1. National Institutes of Health [GM 25439]
  2. Robert A. Welch Foundation
  3. Pfizer, Inc.
  4. Merck Research Laboratories
  5. Boehringer Ingelheim Pharmaceuticals

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The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.

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