Optical Resolution and Determination of Absolute Configuration of (±)-2-[4-(2-Oxocyclopentylmethyl) phenyl] propionic Acids

Abstract

The title compound, which was newly synthesized, showed good anti-inflammatory and analgesic activities. Optical resolution was performed by the following procedures : 1) condensation of the acid with (-)-1-phenylethylamine followed by separation of diasteromeric amides ; 2) reduction of the cyclopentanone moiety and then acylation with optically active acid ; 3) separation of epimeric esters followed by saponification of esters ; 4) oxidation of alcohols to ketones ; 5) saponification of amides. The absolute configurations of the four optically active compounds thus obtained were confirmed by circular dichroism spectroscopy.