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The constitutions of cevine and some related alkaloids

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Zusammenfassung

Die sauerstoffreichen Veratrum-Alkaloide gewinnen in letzter Zeit als blutdrucksenkende Arzneimittel immer mehr an Bedeutung. Darüber hinaus erwecken sie ein grosses Interesse vom Standpunkt des organischen Chemikers, da sie zu den kompliziertest gebauten niedrig molekularen Naturstoffen gehören.

Bei der Konstitutionsaufklärung des Alkamins Cevin (XXXII), das eine Schlüsselstellung in dieser Reihe einnimmt, wurden unter anderem die folgenden neuen Ergebnisse erhalten:

  1. a)

    Die Konstitution zweier Abbauprodukte des Cevins — der Decevinsäure (XIII) und der « Hexan-tetracarbonsäure » (XVIII) — konnte bestimmt werden.

  2. b)

    Das sogenannte Anhydrocevin wurde als ein Orthoazetat XLII erkannt.

  3. c)

    Das Cevadin [XLI,R=CH3CH=C(CH3)CO], aus dem das Cevin durch alkalische Hydrolyse entsteht, gab bei milder Oxydation mit Chromsäure durch spontane Zyklisation des entstandenen Zwischenproduktes XLVII ein 7-Oxy-hydrindanon-(1)-Derivat (XLVI).

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Author information

Authors and Affiliations

  1. Birkbeck College, University of London, UK

    D. H. R. Barton

  2. Organisch-chemisches Laboratorium, Eidg. Technische Hochschule, Zürich

    O. Jeger & V. Prelog

  3. Converse Memorial Laboratory, Harvard University, Cambridge, Mass., U.S.A.

    R. B. Woodward

Authors
  1. D. H. R. Barton
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  2. O. Jeger
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  3. V. Prelog
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  4. R. B. Woodward
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Additional information

We wish to express our cordial appreciation to our collaborators: Messrs.C. J. W. Brooks, J. S. Fawcett, andP. de Mayo (London),F. Gautschi, E. Kyburz, M. V. Mijović, E. Sundt, andCh. Vogel (Zürich) andR. Mirza (Cambridge) for their participation in the work summarized in this article. The experimental material, in so far as it has not already been published, will be presented in due course in papers in the Helv. chim. Acta and J. Chem. Soc.

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Barton, D.H.R., Jeger, O., Prelog, V. et al. The constitutions of cevine and some related alkaloids. Experientia 10, 81–90 (1954). https://doi.org/10.1007/BF02158513

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