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

(1R,2R,3S, 4S)-4-Amino-3-hydroxy-1,2-epoxybutanes, accessible in four steps from L-aminoesters, react regio- and stereoselectively with diethyl alumin um cyanide to give (1R, 2S, 3S, 4S)-4-amino-2,3-dihydroxynitriles. Hydrolys is yields hydroxylactones equivalent to 2,3-dihydroxy-4-aminoacids. The seq uence provides a novel approach to dihydroxyethylene isosteres potentially useful for new HIV-protease inhibitors. (C) 1999 Elsevier Science Ltd. All rights reserved.