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Digitale Medien

Ein einfacher Zugang zu den tetracyclischen Vorläufern der Hetero- und Secoyohimbane, Strychnos- und Oxindolalkaloide (1994)

Rosenmund, Peter ; Hosseini-Merescht, M. ; Bub, Christoph

Weinheim : Wiley-Blackwell

Liebigs Annalen 1994 (1994), S. 151-158

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ISSN: 0170-2041

Schlagwort(e): Indoles ; Alkaloids ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: A Simple Entry into the Series of Tetracyclic Hetero- and Secoyohimbanes, Strychnos and Oxindole AlkaloidsThe divinylogous urethane 4a reacts in diluted acetic acid to give the indolochinolizine 9 (yield 40%). The total amount grows up to 65%, if compound 14, prepared from 4a in nearly quantitative yield, is allowed to react with trifluoroacetic acid for a few minutes. Similarily, 4b and 4c give by treatment with SnCl2 and heat in an [4+2]-cycloaddition reaction the spiroindolines 17 and 18. Oxytryptamine reacts with 2 moles of 2 to give immediately the spirooxindole 21. This compound can be rearranged to give 23 (after treatment with acid, reduction and catalytic hydrogenation). 23 has the cis-configuration of rhyncophylline.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.199419940208

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