Synthesis of homoerythrinadienone by phenolic oxidative coupling

Abstract

Oxidation of N-(3-hydroxy-4-methoxyphenethyl)-3-(3-hydroxy-4-methoxyphenyl)propylamine (VII) with potassium ferricyanide gave homoerythrinadienone. Our tentatively proposed structure (VIII){6,7,9,10-tetrahydro-12-hydroxy-2,13-dimethoxy-14bH-dibenzo[h,j]quinolizin-3(5H)-one} should be revised to (IX){6,8,9,10-tetrahydro-12-hydroxy-2,13-dimethoxy-14bH-indolo[7a,1-a][2]benzazepin-3(5H)-one}. Phenolic oxidation of N-(3-hydroxy-4-methoxyphenethyl)-3-(3-hydroxy-2,4-dimethoxyphenyl)propylamine is also described.