AN APPROACH TO THE SKELETON OF YOHIMBINE-TYPE ALKALOIDS VIA MANNICH-MICHAEL 
REACTIONS WITH INDOLYLETHYLIMINES

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

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AN APPROACH TO THE SKELETON OF YOHIMBINE-TYPE ALKALOIDS VIA MANNICH-MICHAEL REACTIONS WITH INDOLYLETHYLIMINES

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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. (1991). AN APPROACH TO THE SKELETON OF YOHIMBINE-TYPE ALKALOIDS VIA MANNICH-MICHAEL REACTIONS WITH INDOLYLETHYLIMINES. SYNLETT, (12), 881-884.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9AE4-1

Abstract

Schiff bases derived from tryptophane methyl ester and tryptamine react with Danishefsky's diene [1-methoxy-3-(trimethylsiloxy)-1,3-butadiene] in the presence of zinc(II) chloride to give enaminones (1-[2-(indol-3-yl)ethyl]-4-oxo-1,2,3,4-tetrahydropyridines), which are subsequently transformed into indolo[2,3-a]quinolizidin-2-ones (1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo[2,3-a]quinolizines) by acid-catalyzed cyclization.