High diastereo- and enantio-selectivity 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-lyxo-hexopyranoside, 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%.