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Communication | Regular issue | Vol 4, No. 10, 1976, pp.1637-1644
Published online, 1st January, 1970
DOI: 10.3987/R-1976-10-1637
Photooxygenation of 9-Keto-7-methoxy-6-methyl-9H-pyrrolo[1,2-a]indole as a Synthetic Approach to the Mitomycins

Tetsuji Kametani,* Tatsushi Ohsawa, Kimio Takahashi, Masataka Ihara, and Keiichiro Fukumoto

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

Abstract

Sensitized photooxidation in methanol of 9-keto-7-methoxy-6-methyl-9H-pyrrolo[1,2-a]indole (9), prepared from 2-bromo-5-methoxy-4-methylbenzaldehyde (5) via 2-(2-bromo-5-methoxy-4-methylbenzoyl)pyrrole (8), afforded 9,9a-dihydro-3-hydroperoxy-9-keto-7,9a-dimethoxy-6-methyl-3H-pyrrolo[1,2-a]indole (11) and the 3-hydroxy compound (12), the latter of which is considered as a potential precursor of the mitomycins.