Chemical and Enzymic Phenol Oxidation of (R) (-)-N-Methylcoclaurine and (S) (+)-Reticuline : Studies on the Syntheses of Heterocyclic Compounds. CMII

Abstract

Phenol oxidation of (R) (-)-N-methylcoclaurine (V) and (S) (+)-reticuline (VI) with peroxidase was examined in order to get the bisbenzylisoquinoline type compounds, but only the cleaved products were obtained. (±)-O-Benzyl-N-methylcoclaurine (X) also afforded the cleaved one in the same reaction. However, ferricyanide oxidation of VI gave isoboldine (IX) and pallidine (VIII) together with the cleaved products, isovanillin (XIV) and thalifoline (VII). Moreover, phenol oxidation of cuspidaline (XVII) was also described.