Synthesis of dihydrobenzofuranone derivatives with biotechnological methods

Abstract

Benzofuranone derivatives have important skeletons which are widely present in various biologically active molecules, thus, synthesis of optically pure compounds presents great interest for medicinal chemistry. In our study, the enantioselective synthesis of 4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-5-yl acetate (3) and 4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-5-ol derivative (4) was achieved for the first time. Several lipases were used for the kinetic resolution of different pH values and different solvent systems of racemic 4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-5-yl acetate (rac-3) in which the lipases from HPL, PPL, RNL and PCL displayed high enantioselectivity towards 4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran-5-ol derivative (4) at pH=7.