Studies on the syntheses of heterocyclic compounds. Part CCCXCIII. Synthesis of norerythrinadienone by phenolic oxidative coupling

Abstract

Oxidation of N-(3-hydroxy-4-methoxybenzyl)-3-hydroxy-4-methoxyphenethylamine (6) with potassium ferricyande gave norerythrinadienone (3), which was converted into 6-acetyl-5,6,7,8-tetrahydro-2,3,10,11-tetramethoxydibenz[c,e]azocine (15). N-Acetyl-N-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-3-methoxyphenethylamine (19) was oxidised to afford the corresponding dienone (20), which was transformed into compound (15)via the triacetate (21).