Optically Active 9,10-Dihydro-9,10-etheno and -ethanoanthracenes. I. Syntheses of Optically Active 1,5-Disubstituted-9,10-dihydro-9,10-etheno and -ethanoanthracenes.

Abstract 1,5-Dimethoxycarbonyl-9,10-dihydro-9,10-ethenoanthracene was synthesized by the reaction of 1,5-dimethoxycarbonylanthracene with dichloroethylene followed by dechlorination with zinc-copper couple. Optical resolution of l,5-dicarboxy-9,10-dihydro-9,10-ethenoanthracene prepared from the dimethyl ester could be achieved by strychnine to give optically pure (−)-dicarboxylic acid and (+)-diacid with an optical purity of 87.3%. Catalytic reduction of (−)-dicarboxylic acid afforded (−)-ethano-dicarboxylic acid. Transformation of the carboxyl groups in various substituent groups to give optically active C2-symmetrical etheno- and ethanoanthracene derivatives belonging to the same series of absolute configuration as that of the starting material is described.