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We describe here the first total synthesis of two tetrasubstituted 1,2,3,4-tetrahydronaphtho[2,1f]isoquinolines (8,9,11,12-tetramethoxy-2-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline and 8,9,11-trimethoxy-2-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolin-12-ol). The key steps were the Bischler-Napieralski cyclization of ethyl (2-{2-[2-(3,4-dimethoxyphenyl)vinyl]4,5-dimethoxyphenyl}ethyl)methylcarbamates to form the isoquinoline units and photocyclization of the resulting 5-[2-(3,4-dimethoxyphenyl)vinyl]-7,8-dimethoxy-2-methyl-3,4dihydroisoquinolin-1(2H)-ones to 8,9,11,12-tetramethoxy-2-methyl-3,4-dihydronaphtho[2,1f]isoquinolin-1(2H)-ones.

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Total synthesis of 8,9,11,12-tetramethoxy-2-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline and 8,9,11-trimethoxy-2-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolin-12-ol