Practical synthesis of a key intermediate for lactacystin from (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate

Chem Pharm Bull (Tokyo). 2008 May;56(5):738-41. doi: 10.1248/cpb.56.738.

Abstract

A practical synthesis of a key intermediate for the proteasome inhibitor lactacystin from (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate was established. (R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate is a useful chiral building block for the synthesis of biologically active compounds containing alpha-substituted alpha-amino acid moieties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcysteine / analogs & derivatives*
  • Acetylcysteine / chemical synthesis
  • Chromatography, High Pressure Liquid
  • Cysteine Proteinase Inhibitors / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oxazoles / chemical synthesis*
  • Solvents
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared

Substances

  • (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate
  • Cysteine Proteinase Inhibitors
  • Indicators and Reagents
  • Oxazoles
  • Solvents
  • lactacystin
  • Acetylcysteine