Preparation of (2R,3S)-(-)- and (2S,3R)-(+)-2,3-Epoxy-2-methylbutanoic Acids and Some of Their Esters

Article abstract of DOI:10.1016/0957-4166(95)00205-4

Enantiomerically pure (2R,3S)-(-)- and (2S,3R)-(+)-2,3-epoxy-2-methylbutanoic acids 7 and 8 were prepared from 2-methyl-2-butenoic acid 1 (tiglic acid).They were characterized by spectroscopic and optical activity data and their absolute configuration was determined by chemical correlation with (R)-(+)- and (S)-(-)-2-methyl-1,2-butanediols.The corresponding methyl (16 and 17), menthyl (3 and 4), and 9α-angeloyloxy-1-oxolongipin-2-en-7β-yl (14 and 15) esters were also prepared.