STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES

N-protected alpha-amino epoxides of erythro configuration, derived fro m alpha-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S) configuration was achieved by the synthetic sequence: amino acid -> haloketone -> halohydrin -> epoxide. A mechanistic expl anation for the observed stereoselectivity is presented. This stereose lective synthetic approach was applied to the synthesis of a variety o f short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.