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The basicity and steric configuration of the diterpene alkaloids veatchine and atisine

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Zusammenfassung

Die Basizität und das verschiedene chemische Verhalten der Isomerenpaare Veatchin-Garryin und Atisin-Isoatisin werden mit der sterischen Konfiguration dieser Verbindungen in Zusammenhang gebracht.

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Literatur

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  4. We thank ProfessorCarl Djerassi for bringing up this possibility in a discussion at the Sixth Summer Seminar, University of New Brunswick, August 1954.

  5. Both garryine and veatchine give salts which still retain their different identities as characterized most conveniently by potentiometric titration. ThepK value found by titration of garryine and veatchine hydrochlorides are identical with those found by the titration of the free bases. Again, basification of a solution of veatchine and garryine hydrochlorides leads to isolation of pure veatchine and garryine respectively, and not to the isolation of an equilibrium mixture of the same composition in both cases, as might be expected if the above assumption was correct.

  6. K. Wiesner, R. Armstrong, M. F. Bartlett, J. A. Edwards, J. A. C. S.76, 4858 (1954); Chem. and Ind.1954, 132.

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  7. This follows clearly from the interrelations given in our last paper (K. Wiesner, R. Armstrong, M. F. Bartlett, J. A. Edwards, J. A. C. S.76, 4858 (1954); Chem. and. Ind.1954, 132).

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  10. For a summarising reference seeE. S. Stern inR. H. F. Manske andH. L. Holmes,The Alkaloids, Vol. 4 (Academic Press Inc., New York, 1955).

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  11. See alsoM. F. Bartlett, Ph. D. Thesis, University of New Brunswick, May 1954.

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Authors and Affiliations

  1. Converse Memorial Laboratories, Harvard University, Cambridge, Mass., USA

    K. Wiesner & J. A. Edwards

  2. University of Brunswick, Fredericton, New Brunswick, Canada

    K. Wiesner & J. A. Edwards

Authors
  1. K. Wiesner
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  2. J. A. Edwards
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Wiesner, K., Edwards, J.A. The basicity and steric configuration of the diterpene alkaloids veatchine and atisine. Experientia 11, 255–259 (1955). https://doi.org/10.1007/BF02161241

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