On the Synthesis of Protopine Alkaloids
The Journal of Organic Chemistry2007Vol. 72(19), pp. 7301–7306
Citations Over TimeTop 17% of 2007 papers
Yasuhiro Wada, Harumi Kaga, Shiho Uchiito, Eri Kumazawa, Miho Tomiki, Yu Onozaki, Nobuhito Kurono, Masao Tokuda, Takeshi Ohkuma, Kazuhiko Orito
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 alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined.
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