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Journal Article

Construction of Tetracyclic Indole Bases Via Aza-Diels-Alder Reaction of Indolylethylimines with Brassard's Diene

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Lock, R., & Waldmann, H. (1993). Construction of Tetracyclic Indole Bases Via Aza-Diels-Alder Reaction of Indolylethylimines with Brassard's Diene. Natural Product Letters, 2(1), 49-56. doi:10.1080/10575639308043454.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-9D0C-4
Abstract
Schiff bases derived from tryptamine react with Brassard's diene in the presence of EtAlCl2 to give functionalised 1,2,5,6-tetrahydropyridines which are subsequently transformed to indolo[2,3-a]quinolizines by Bischler-Napieralski reaction and reduction of the intermediate iminium salts with NaBH4.