ISOQUINOLINE ALKALOIDS - 3 - SYNTHESIS OF THE 6-ETHYL AND 6-BUTYL ANALOGS OF O-1,2,9,10-TETRAMETHOXY-4H-DIBENZO[DE,G]-QUINOLINE 1.5 PHOSPHATE (D,L-GLAUCINE 1.5 PHOSPHATE)

The syntheses of the 6-ethyl (12b) and 6-butyl (12c) analogs of d,l-gl aucine 1.5 phosphate (12a) in 10 steps from papaverine hydrochloride ( 1) are described, Mechanistic rationale for the formation of Hofmann d egradation products observed during the methylation of the 6 ethyl (7b ) and 6-butyl (7c) analogs of d,l-1,2,9,10-tetrahydroxyaporphine (7a) with phenyltrimethylammonium hydroxide are discussed, Detailed analyse s and assignments of the H-1 and C-13 NMR spectra of 12a-c and the cor responding free base forms 8a-c are presented.