HIGH DIASTEREO-SELECTIVITY AND ENANTIOSELECTIVITY IN THE ENZYMATIC-HYDROLYSIS OF A RACEMIC ANHYDRODEOXYSUGAR - A TOTALLY SYNTHETIC APPROACH TO BOTH ENANTIOMERS OF BOIVINOSE

Abstract

The microsomal epoxide hydrolase-promoted hydrolysis of racemic isobutyl 3,4-anhydro-2,6-dideoxy-β-lyxohexopyranoside, which is easily prepared from isobutyl vinyl ether and but-3-en-2-one, occurs with very high regio-and enantio-selectivity, with kinetic resolution leading to the L-and D-forms of isobutyl β-boivinoside, both with an enantiomeric excess of at least 96%