Syntheses of a proerythrinadienone by phenolic oxidation and a morphinandienone system by a photo-pschorr reaction

Abstract

Phenolic oxidative coupling of ethyl 1,2,3,4-tetrahydro-6-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-7-methoxyisoquinoline-2-carboxylate (2c) with potassium ferricyanide afforded the indenoisoquinoline (3c), which rearranged on treatment with acid. Spectral data, and methylation of the rearrangement product and comparison with the dienone (22) obtained from the diazotisation of the aminobenzylisoquinoline (15), followed by photolysis, excluded the morphinan structure (12), and confirmed the dibenz[d,f]indole structure (13).