Imine (III) was prepared by condensation of 6-methoxy-1-tetralone (I) with p-aminophenol (II) at 180 C. After silylation of the hydroxyl group of (III) with tert-butyldimethylsilyl chloride to give (IV), acylation of the enamine function with 2-bromo-5-methoxybenzoyl chloride (V) yielded enamide (VI). Halogenation of (VI) with N-bromosuccinimide gave the beta-bromo enamide (VII). Photocyclization of (VII) produced the benzophenanthridine (VIII), which was further dehydrogenated with DDQ providing (IX). Desilylation of (IX) to afford phenol (X) was achieved by treatment with hydrogen fluoride-pyridine.

Condensation of phenol (X) with N-(2-hydroxyethyl)piperidine (XI) under Mitsunobu conditions furnished ether (XII). The lactam function of (XII) was then reduced with LiAlH4 to produce (XIII). Finally, methyl ether cleavage in (XIII) was carried out by treatment with AlCl3 in the presence of EtSH.