Studies on the syntheses of heterocyclic compounds. Part CD. Total syntheses of NO(10)-dimethylhernovine and kreysigine by photolysis of diazotised isoquinolines

Abstract

Photolysis of the diazonium salt (6) from 1-(2-amino-3,4-dimethoxybenzyl)-6-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline (5) gave the morphinandienone (2) and the aporphine (26), which on debenzylation afforded NO(10)-dimethylhernovine (27). Similar treatment of the diazonium salt (13) from 1-(2-amino-3,4,5-trimethoxyphenethyl)-1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinoline (12) furnished kreysigine (20) and O-methylandrocymbine (17).