4.8 Article

Intramolecular Diels-Alder Cycloaddition/Rearrangement Cascade of an Amidofuran Derivative for the Synthesis of (±)-Minfiensine

Journal

ORGANIC LETTERS
Volume 13, Issue 15, Pages 3767-3769

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201320v

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Funding

  1. National Science Foundation [CHE-1057350]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [1057350] Funding Source: National Science Foundation

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An efficient synthesis of (+/-)-minfiensine has been accomplished employing an intramolecular Diels-Alder cycloaddition/rearrangement cascade of an amidofuran derivative. Thermal reorganization of the Initially formed [4 + 2]-cycloadduct affords the critical tetrahydroiminoethanocarbazole skeleton of the alkaloid in high yield.

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