Enantioselective synthesis of BMS-204352 (MaxiPost) using N-fluoroammonium salts of cinchona alkaloids (F-CA-BF4)

Org Biomol Chem. 2003 Jun 7;1(11):1833-4. doi: 10.1039/b303113f.

Abstract

The enantioselective synthesis of a potent Maxi-K potassium channel opener (BMS-204352) mediated by N-fluoroammonium salts of cinchona alkaloids is described. Two synthetic pathways were evaluated. An ee as high as 88% was achieved (>99% after a single recrystallisation).

MeSH terms

  • Cinchona Alkaloids / chemistry*
  • Hydrocarbons, Fluorinated / chemistry
  • Indoles / chemical synthesis*
  • Quaternary Ammonium Compounds / chemistry
  • Stereoisomerism

Substances

  • BMS204352
  • Cinchona Alkaloids
  • Hydrocarbons, Fluorinated
  • Indoles
  • Quaternary Ammonium Compounds