Abstract
Oxidation of diterpene alkaloids by dimethyldioxirane was studied with eldeline, talatizamine, aconitine, and zongorine as examples. Nitrones and 19-oxo derivatives of bases were obtained. The results of the oxidation allow one to draw an analogy with the oxidation by KMnO4 and to suggest a mechanism of the reaction.
Similar content being viewed by others
References
R. W. Murray, Chem. Rev., 1989, 89, 1187.
R. W. Murray, R. Jearand, and L. Mohan, Tetrahedron Lett., 1986, 27, 2335.
R. W. Murray, S. N. Rajadhyaksha, and L. Mohan, J. Org. Chem., 1989, 54, 5783.
J. K. Grandall and T. Reix, J. Org. Chem., 1992, 57, 6759.
W. Adam and L. Hadjiarapoglou, in Topics Current Chemistry, Ed. W. A. Herrman, Springer Verlag, Berlin-Heidelberg, 1993, 164, 45.
R. W. Murray and M. Singh, Synth. Commun., 1989, 19, 3509.
R. W. Murray and M. Singh, Magnetic resonance in chemistry, 1991, 29, 962.
R. W. Murray and M. Singh, J. Org. Chem., 1990, 55, 2954.
R. W. Murray and M. Singh, Tetrahedron Lett., 1988, 29, 4677.
W. Adam, K. Briviba, F. Duscher, D. Golsch, W. Kiefer, and H. Sies, J. Chem. Soc., Chem. Commun., 1995, 1831.
M. Ferrer, F. Sanchez-Baeza, A. Messeguer, A. Diez, and M. Rubiralta, J. Chem. Soc., Chem. Commun., 1995, 293.
P. C. Buxton, J. N. Ennis, B. A. Marples, V. L. Waddington, and T. R. Boehlou, J. Chem. Soc., Perkin Trans. 2, 1998, 265.
O. Achmatowiez Jr., Y. Tsuba, and Leo Marion, Can. J. Chem., 1965, 43, 2336.
V. E. Zubarev, V. N. Belevskii, and L. T. Bugaenko, Usp. Khim., 1979, 48, 1361 [Russ. Chem. Rev., 1979, 48 (Engl. Transl.)].
Khimiya i khemilyuminestsentsiya dioksiranov [Chemistry and Chemiluminescence of Dioxiranes], Ed. Yu. N. Bubnov, Nauka, Moscow, 1999, 93 (in Russian).
K. Wiesner, M. Gotz, D. L. Simmons, and L. R. Fowler, Tetrahedron Lett., 1959, 15.
S. A. Osadchii, N. A. Pankrushina, M. M. Shakirov, E. E. Shul'ts, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2000, 49, 552 [Russ. Chem. Bull., Int. Ed., 2000, 49, 557].
C. F. Grabovskii, N. N. Kabal'nova, S. L. Khursan, and V. V. Shereshovets, Izv. Akad. Nauk, Ser. Khim., 1998, 47, 1321 [Russ. Chem. Bull., 1998, 47, 1284 (Engl. Transl.)].
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zinurova, E.G., Kabal"nova, N.N., Shereshovets, V.V. et al. Oxidation of diterpenoid alkaloids with dimethyldioxirane. Russian Chemical Bulletin 50, 720–723 (2001). https://doi.org/10.1023/A:1011385500970
Issue Date:
DOI: https://doi.org/10.1023/A:1011385500970