Synthesis of optically Active Deoxytazettine Neomethine

Abstract

The structure of deoxytazettine neomethine (I), derived from tazettine (III) via 5 steps, was confirmed by synthesis of its optically active and racemic forms. A key step in the synthesis, conversion of 2'-bromomethyl-4', 5'-methylenedioxy-2-biphenylcarbal-dehyde (VI) to 7-cyano-5, 7-dihydro-2, 3-methylenedioxydibenz [c, e] oxepin (VII), was achieved by employing a novel method which had been developed for synthesis of 5-cyano-5, 7-dihydrodibenz [c, e] oxepin (V). The nuclear magnetic resonance spectra of the neomethine (I) and its synthetic intermediates were discussed.