Studies on the syntheses of heterocyclic compounds. Part CCCI. Biogenetic syntheses of the morphinandienone-type compounds, isosalutaridine and O-methylflavinantine

Abstract

Phenolic oxidative coupling of (±)-reticuline (I) with potassium ferricyanide afforded isoboldine (III) and iso-salutaridine (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).