4.8 Article

Total Synthesis of (-)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2+2+2] Cyclization between Ynamide and Diynes

Journal

ORGANIC LETTERS
Volume 14, Issue 7, Pages 1914-1917

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300571b

Keywords

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Funding

  1. JSPS [23390001]
  2. MEXT, Japan [23105501]
  3. Fugaku Trust for Medicinal Research
  4. NOVARTIS Foundation (Japan)
  5. Takeda Science Foundation
  6. Grants-in-Aid for Scientific Research [24790002, 23390001] Funding Source: KAKEN

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The total syntheses of (-)-herbindoles A, B, and C as naturally occurring forms were accomplished for the first time through transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes. This strategy provided a highly efficient synthetic route to all three herbindoles from an identical indoline derivative as a common intermediate.

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