Abstract:
Sodium and liquid ammonia reduction of hayatinin ethyl ether affords a non-phenolic component, identified as dl-4'-O-methyl-7-0-ethyl-N-methylcoclaurine, and a phenolic component identified as dl-N- ethylcoclaurine. The structures of these two fragments have been confirmed by nuclear magnetic resonance and mass spectral data as well as the synthesis of the former by usual methods. This establishes the structure of hayatinin as 4"-O-methyl-bebeerine proposed earlier by Bhattacharji et al. [J. scient. indo Res., 21B (1962), 428]. The optical inactivity of hayatinin as well as of phenolic and non-phenolic fragments suggests that hayatinin isolated from this plant is a racemic mixture.
