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

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.

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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; CHIRAL AUXILIARIES; AQUEOUS-SOLUTION; BENZYL ESTER
 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.

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Language(s): eng - English
 Dates: 1991-12
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: A1991GX76300014
 Degree: -

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Title: SYNLETT
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: STUTTGART : GEORG THIEME VERLAG
Pages: - Volume / Issue: (12) Sequence Number: - Start / End Page: 881 - 884 Identifier: ISSN: 0936-5214