4.8 Article

Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine

Journal

ORGANIC LETTERS
Volume 13, Issue 1, Pages 138-141

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102709s

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Funding

  1. NTH Neurological Disorders & Stroke Institute [NS-12389]
  2. National Institute of General Medical Sciences [GM-098601]
  3. UC Irvine Chancellor's Fellowship
  4. Bristol-Myers Squibb
  5. Amgen
  6. Alexander von Humboldt Foundation

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The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates.

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