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

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-9C15-5 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-9C1A-C
Genre: Journal Article

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 Creators:
Waldmann, Herbert1, Author           
BRAUN, M2, Author
WEYMANN, M2, Author
GEWEHR, M2, Author
Affiliations:
1Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              
2external, ou_persistent22              

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Free keywords: DIELS-ALDER REACTIONS; AMINO-ACID ESTERS; PICTET-SPENGLER REACTION; CHIRAL AUXILIARIES; AQUEOUS-SOLUTION; BENZYL ESTER; CYCLOADDITIONS
 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.

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Language(s): eng - English
 Dates: 1993
 Publication Status: Issued
 Pages: 20
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: ISI: A1993KD05700012
DOI: 10.1016/S0040-4020(01)80309-4
 Degree: -

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Title: TETRAHEDRON
Source Genre: Journal
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Publ. Info: KIDLINGTON, OXFORD : PERGAMON-ELSEVIER SCIENCE
Pages: - Volume / Issue: 49 (2) Sequence Number: - Start / End Page: 397 - 416 Identifier: ISSN: 0040-4020