Zusammenfassung
Die Massenspektren und1H- und13C-NMR-Spektren der Gelsemium-Alkaloide Gelsemin, Gelsedin und Gelsevirin wurden aufgenommen und vollständig analysiert. Gelsevirin wurde durch Reduktion in Gelsemin übergeführt und besitzt die Struktur des Na-Methoxygelsemins.
References
H. Schwartz andL. Marion, Can. J. Chem.31, 958 (1953) and references therein.
The authors are indebted to the Mass Spectrometry Laboratory of the Batelle Memorial Institute for the high-resolution spectrum and element map.
For a description of a 60 MHz PMR spectrum of gelsemine seeH. Conroy andJ. K. Charkabarti, Tetrahedron Lett.4, 6 (1959).
The remainder of the spectrum of gelsedine (2a), except for the oxymethylene signal [4.19 (d, J=11.0 Hz), 4.27 (dd, J=11.0, 4.0 Hz)] was nearly as ambiguous as the reported 60 MHz spectrum [E. Wenkert, J. C. Orr, S. Garratt, J. H. Hansen, B. Wickberg andC. L. Leicht, J. Org. Chem.27, 4123 (1962)].
E. Wenkert, C.-J. Chang, A. O. Clouse andD. W. Cochran, Chem. Commun.1970, 961.
C. W. Moore, J. chem. Soc.99, 1231 (1911). —R. Goutarel, M.-M. Janot, V. Prelog andR. P. A. Sneeden, Helv. chim. Acta34, 1962 (1951). —V. Prelog, J. B. Patrick andB. Witkop, Helv. chim. Acta35, 640 (1952).
On the assumption of Lewis acid-base complexation affecting the chemical shifts the previous CMR spectrum of gelsemine (1a)6, run at ca. 1.5M concentration, was not used for the comparison study. Further, the former spectrum was recorded on a continuous wave spectrometer, while the present study utilized a Fourier Transform spectrometer.
For an X-ray analysis of gelsemicine (2b) seeM. Przybylska andL. Marion, Can. J. Chem.39, 2124 (1961). —M. Prezybylska, Acta Crystallogr.15, 301 (1962).
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U.S. Public Health Service predoctoral fellow, 1967–1971.
This communication represents paper VIII of the series ‘Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Naturally Occurring Substances’. For the preceding article seeE. Wenkert, D. W. Cochran, E. W. Hagaman, R. B. Lewis andF. M. Schell, J. Am. chem. Soc.93, 6271 (1971).
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Wenkert, E., Chang, C.J., Cochran, D.W. et al. The structure of gelsevirine. Experientia 28, 377–379 (1972). https://doi.org/10.1007/BF02008283
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DOI: https://doi.org/10.1007/BF02008283