13C nuclear magnetic resonance spectroscopy of atisine and veatchine-type C20-diterpenoid alkaloids from aconitum and garrya species

Tetrahedron
1978.0

Abstract

13C NMR spectra of the atisine- and veatchine-type alkaloids, as well as certain of their derivatives, have been obtained by the Fourier transform technique at 25.03 MHz. With the help of single-frequency off-resonance proton decoupling techniques, additivity relationships, and the effects induced by certain structural changes, self-consistent assignments of nearly all the resonances have been made. The 13C NMR spectra are also analyzed to identify skeletal features of the atisine and veatchine-type alkaloids of use in the structure determination of new C20-diterpenoid alkaloids. On the basis of the 13C NMR analysis of atisine and veatchine as well as a temperature-dependence study of atisine, the existence of C-20 epimers in these alkaloids is demonstrated. A 13C NMR study of the behavior of the oxazolidine ring of atisine in non-ionic and ionic solvents indicates that the C-20 epimers of atisine do not exist in an equilibrium mixture in solution and are not interconvertible via a zwitterion as reported earlier. © 1978.

Knowledge Graph

Similar Paper

13C nuclear magnetic resonance spectroscopy of atisine and veatchine-type C20-diterpenoid alkaloids from aconitum and garrya species
Tetrahedron 1978.0
<sup>13</sup>C Nuclear magnetic resonance spectroscopy in the elucidation of structures of diterpenoid alkaloids
Canadian Journal of Chemistry 1987.0
Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XIX. Aspidosperma alkaloids
Journal of the American Chemical Society 1973.0
N-Oxides of Some Norditerpenoid Alkaloids
Journal of Natural Products 1995.0
Developments in the Chemistry of Diterpenoid Alkaloids
Journal of Natural Products 1980.0
Assignment of the 13C N.M.R. Spectra of Some 22,26-Epiminocholestanes 22,26-Epiminocholest-22(N)-enes and Some 3β-Amino Steroidal Alkaloids
Australian Journal of Chemistry 1979.0
<b>Alkaloid Studies. XXXVI.</b><sup>1</sup> <b>The Complete Absolute Configuration of the Diterpene Alkaloids of the <b><i>Garrya</i></b> and Atisine Groups and their Direct Correlation with the Phyllocladene-type Diterpenes</b><sup>2</sup>
Journal of the American Chemical Society 1962.0
13C-NMR studies on the cevanine alkaloids : the application of 13C-NMR spectrum for structure elucidation of new alkaloids, baimonidine and isoverticine
Tetrahedron Letters 1979.0
The structures of cardionine and 11-acetylcardionine, new C20-diterpenoid alkaloids, from the selective INAPT NMR technique
The Journal of Organic Chemistry 1990.0
Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry of Solanidine, Leptinidine, and Acetylleptinidine. Steroidal Alkaloids from <i>Solanum chacoense</i> Bitter
Journal of Agricultural and Food Chemistry 1997.0