STUDIES ON SYNTHESES OF HETEROCYCLIC COMPOUNDS .301) BIOGENETIC SYNTHESES OF MORPHINANDIENONE-TYPE COMPOUNDS, ISOSALUTARIDINE AND O- METHYLFLAVINANTINE

Phenolic oxidative coupling of (±)-reticuline (I) with potassium ferricyanide afforded isoboldine (III) and isosalutaridine (VIII), which were methylated with diazomethane to give glaucine (IV) and O-methylflavinantine (XII), respectively. This work also implies formal biogenetic syntheses of amurine (IX) and flavinantine (X), which are biogenetically equivalent to isosalutaridine (VIII).