Stereoselective synthesis of non symmetric dihydroxyethylene dipeptide isosteres via epoxy alcohols derived from alpha-amino acids

Bioorg Med Chem Lett. 1999 Oct 18;9(20):3027-30. doi: 10.1016/s0960-894x(99)00529-6.

Abstract

(1R,2R,3S,4S)-4-Amino-3-hydroxy-1,2-epoxybutanes, accessible in four steps from L-aminoesters, react regio- and stereoselectively with diethyl aluminum cyanide to give (1R,2S,3S,4S)-4-amino-2,3-dihydroxynitriles. Hydrolysis yields hydroxylactones equivalent to 2,3-dihydroxy-4-aminoacids. The sequence provides a novel approach to dihydroxyethylene isosteres potentially useful for new HIV-protease inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Amino Acids / chemistry*
  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Dipeptides / chemistry*
  • Epoxy Compounds / chemistry*
  • Ethylenes / chemical synthesis*
  • Ethylenes / chemistry
  • HIV Protease Inhibitors / chemical synthesis*
  • HIV Protease Inhibitors / chemistry

Substances

  • Alcohols
  • Amino Acids
  • Anti-HIV Agents
  • Dipeptides
  • Epoxy Compounds
  • Ethylenes
  • HIV Protease Inhibitors
  • hydroxyethylene