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Communication | Regular issue | Vol 23, No. 7, 1985, pp.1603-1606
Published online, 1st January, 1970
DOI: 10.3987/R-1985-07-1603
A Photochemical Route to Pyrrolo[1,4]benzodiazepine Antitumor Antibiotics

Paul H. Mazzocchi* and Ann DeCamp Schuda

*Department of Chemistry, University of Maryland, College Park, Marykland 20742, U.S.A.

Abstract

The parent pyrrolo[1,4]benzodiazepine ring system was synthesized. The key step was the photostimulated ring expansion reaction of N-pentenylphthalimide to give a pyrrolobenzazepinedione photoproduct. Conversion of the pyrrolobenzazepinedione ring system to the pyrrolo[1,4]benzodiazepine ring system was accomplished in several steps with the key step a Curtius rearrangement.