4.8 Article

Tandem Phenolic Oxidative Amidation-Intramolecular Diels-Alder Reaction: An Approach to the Himandrine Core

Journal

ORGANIC LETTERS
Volume 12, Issue 8, Pages 1760-1763

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1003669

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Funding

  1. University of British Columbia
  2. Canada Research Chair Program
  3. NSERC
  4. CIHR,
  5. MerckFrosst Canada

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An oxidative cyclization of dienic sulfonamides mediated by iodobenzene diacetate in TFA, followed by a tandem intramolecular Die Is Alder reaction, achieves desymmetrization of a locally symmetrical dienone with good levels of diastereoselectivity and leads to valuable synthetic intermediates for the himandrine alkaloids.

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