Synthesis of Dihydrobenzofuranone Derivatives with Biotechnological Methods

Abstract

Benzofuranone derivatives are important structural units in many biologically active compounds thus, synthesis of these types of compounds in optically pure form found increased interest in pharmaceutical chemistry. In this study, the enantioselective synthesis of 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (3) and 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) was carried out for the first time, by enzyme-mediated hydrolysis reactions with high enantiomeric excesses. Several lipases were used for the kinetic resolution in different pH values and different solvent systems of racemic 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (rac-3) in which the lipases from HPL, PPL, RNL and PCL displayed high enentioselectivity towards 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) at pH=7.