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A novel synthesis of benzo- and indolo[a]quinolizidines by intramolecular diels-alder reaction of l-azadienes

✍ Scribed by Masataka Ihara; Tomoko Kirihara; Akihiro Kawaguchi; Keiichiro Fukumoto; Tetsuji Kametani

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 253 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81488-x

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✦ Synopsis

Intramolecular Diels-Alder reaction is one of the most powerful methods for syntheses of polycyclic ring systems with stereocontrol. 1 It is expected that the intramolecular cycloaddition of 1-azadienes2 provides a useful tool for the construction of quinolizidines and indolizidines, common frameworks of many alkaloids. However only few examples 3,4 are so far known mainly due to the difficult formation of 1-azadienes and its scarce reactivity. We have investigated the formation of such systems from a,8-unsaturated amides and the subsequent cycloaddition. Here a novel and facile synthesis of benzo-and indolo--[alquinolizidines according to this strategy is disclosed.

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