The evaluation of a biogenetically based approach to the synthesis of octahydro-1h-benzofuro[3,2-e]isoquinolines

A potential synthetic route to octahydro-1$\text{H}$-benzofuro 3,2-e]isoquinoline derivatives by intermolecular oxidative phenolic coupling has been studied. A variety of successful coupling reactions have been effected between 2-naphthol or 4-t-butylphenol and p-cresol, 2-(p-hydroxyphenyl)ethanol, 3,4-dimethylphenol, 5-indanol and 6-hydroxytetralin, but 2-acetyl-7-hydroxytetrahydroisoquinoline failed to participate in such reactions.