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ASYMMETRIC-SYNTHESIS OF INDOLO[2,3-A]QUINOLIZIDIN-2-ONES - CONGENERS TO YOHIMBINE-TYPE ALKALOIDS

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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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Waldmann, H., BRAUN, M., WEYMANN, M., & GEWEHR, M. (1993). ASYMMETRIC-SYNTHESIS OF INDOLO[2,3-A]QUINOLIZIDIN-2-ONES - CONGENERS TO YOHIMBINE-TYPE ALKALOIDS. TETRAHEDRON, 49(2), 397-416. doi:10.1016/S0040-4020(01)80309-4.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-9C15-5
Abstract
Schiff bases derived from tryptophan methyl ester and tryptamine react with Danishefkys diene in the presence of ZnCl2 to give enaminones which are subsequently transformed into indolo[2,3-a]quinolizidin-2-ones by acid-catalyzed cyclization. These tetracyclic aminoketones serve as viable intermediates in the construction of complex alkaloids, e. g. reserpine and deserpidine, and analogues thereof.