Download PDF
Synlett 1991; 1991(12): 881-884
DOI: 10.1055/s-1991-20910
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

An Approach to the Skeleton of Yohimbine-Type Alkaloids via Mannich-Michael Reactions with Indolylethylimines

Herbert Waldmann* , Matthias Braun, Markus Weymann, Markus Gewehr
  • *Universität Bonn, Institut für Organische Chemie and Biochemie, Gerhard-Domagk-Str. 1, D-5300 Bonn, Germany
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >