Abstract
dl-1, 2-Methylenedioxy-9, 10, 11-trimethoxyaporphine (I) was synthesized by the route shown in Chart 1. The ultraviolet spectrum of (I), as shown in Fig. 1, showed a specific absorptions for an aporphine-type bases in general, similar to those of stephanine, crebanine, and allied bases prepared to date. In the Pschorr reaction for phenanthrene cyclization during this synthesis, a by-product was obtained besides the objective (I). This by-product was 2-methyl-6, 7-methylenedioxy-1, 2, 3, 4-tetrahydroisoquinoline (XV) which is assumed to have been formed by cleavage of the aminobenzyl-tetrahydroisoquinoline compound (XIV) into upper and lower fragments. The usual by-product of this Pschorr reaction, the further deaminated benzyltetra-hydroisoquinoline compound, was not obtained.
