The synthesis of homoproaporphine-type compounds by phenolic oxidative coupling

Abstract

Oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxyphenethyl)-6-methoxy-2-methylisoquinoline (III) with potassium ferricyanide or ferric chloride afforded a homoproaporphine (XIII) in good yield by coupling the 8-position of the isoquinoline to the 1-position of the phenethyl group. The syntheses of (III) and its 1-(3-hydroxy-4,5-dimethoxyphenethyl) analogue (IV) are also described.