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

Waldmann, Herbert; BRAUN, M; WEYMANN, M; GEWEHR, M

doi:10.1016/S0040-4020(01)80309-4

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

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

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Citation

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: https://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.