On the synthesis of protopine alkaloids

Y Wada, H Kaga, S Uchiito, E Kumazawa…

Index: Wada, Yasuhiro; Kaga, Harumi; Uchiito, Shiho; Kumazawa, Eri; Tomiki, Miho; Onozaki, Yu; Kurono, Nobuhito; Tokuda, Masao; Ohkuma, Takeshi; Orito, Kazuhiko Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7301 - 7306

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Citation Number: 15

Abstract

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 ...