Enantioselective fluorination mediated by N-fluoroammonium salts of cinchona alkaloids: first enantioselective synthesis of BMS-204352 (MaxiPost)

J Org Chem. 2003 Mar 21;68(6):2494-7. doi: 10.1021/jo026792s.

Abstract

We have employed a cinchona alkaloid/Selectfluor-mediated enantioselective fluorination of the oxindole 2 to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S-1), an effective opener of maxi-K channels. Fluorination occurred to produce S-1 with 84% ee using the bis-cinchona alkaloid (DHQ)(2)AQN. Recrystallization produced enantiomerically pure (>99% ee) product. Quinidine-mediated fluorination of 2 gave the (R)-antipode of 1 with 68% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Drug Design
  • Fluorine / chemistry*
  • Indicators and Reagents
  • Indoles / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism

Substances

  • BMS204352
  • Cinchona Alkaloids
  • Indicators and Reagents
  • Indoles
  • Quaternary Ammonium Compounds
  • Fluorine