For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno [2, 1-a][3] benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last step for completion of the synthesis. The key substances, indeno [2, 1-a][3] benzazepines, were prepared by Bischler-Napieralski cyclization of ...