Total synthesis of the racemic 3-methyl analogue of the antitumour agent acivicin

Abstract

The racemic 3-methyl analogue (19a) of acivicin (1) has been synthesized by a stereorandom route starting with acetonitrile oxide (3) and a novel vinylglycine precursor, ethyl 2-acetoxybut-3-enoate (9). The diastereoisomeric alcohols (11a,b) and azides (14a,b) were separated and used for the synthesis of the individual diastereoisomers of compounds (10), (12), and (15)–(19). The erythro- and threo-diastereoisomers were identified on the basis of their ¹H and ¹³C n.m.r. spectra.