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Communication | Regular issue | Vol 12, No. 7, 1979, pp.913-916
Published online, 1st January, 1970
DOI: 10.3987/R-1979-07-0913
Synthesis of 1-Benzazocin-5-one Derivatives from a 1,2,3,4-Tetrahydrocyclopent[b]indole; a Synthetic Approach to Mitomycins

Tetsuji Kametani,* Tatsushi Ohsawa, and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Photo-oxygenation of 4-benzyl-1,2,3,4-tetrahydro-5,7-dimethoxy-6-methylcyclopent[b]indole (14), derived from 2,4-dimethoxy-3-methylacetanilide (6) in eight steps, gave, in excellent yield, 1-benzyl-1,2,3,4,5,6-hexahydro-2,5-diketo-8,10-dimethoxy-9-methyl-1-benzazocine (15), which was converted to 1-benzyl-1,2,3,4,5,6-hexahydro-2-keto-5,5,8,10-tetramethoxy-9-methyl-6-methylene-1-benzazocine (19).