Abstract
The oxidation of ecdysteroids and their 7,8-dihydroanalogs with ozone in pyridine occurred regio- and stereoselectively at the hydroxy groups of the A ring giving 2-dehydro-3α-hydroxy derivatives.
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Savchenko, R.G., Urmanova, Y.R., Shafikov, R.V., Afon’kina, S.R., Khalilov, L.M., and Odinokov, V.N., Mendeleev Commun., 2008, vol. 18, p. 191.
Akhrem, A.A. and Kovganko, N.V., Ekdisteroidy: khimiya i biologicheskaya aktivnost’ (Ecdysteroids: Chemistry and Biological Activity), Minsk: Nauka i Tekhnika, 1989, 327.
Dinan, L. and Rees, H.H., Steroids, 1978, vol. 32, p. 629.
Karlson, P., Bugany, H., Döpp, H., and Hoyer, C.A., Z. Physiol. Chem., 1972, vol. 358, p. 1610.
Siddal, J.B., Horn, D.H.S., and Middleton, E.J., Chem. Commun., 1967, p. 899.
Galbraith, M.N., Horn, D.H.S., Middleton, E.J., and Hackney, R.J., Aust. J. Chem., 1969, vol. 22, p. 1517.
Galbraith, M.N., Horn, D.H.S., Middleton, E.J., Thomson, J.A., Siddal, J.B., and Hafferl, W., Chem. Commun., 1969, p. 1134.
Dinan, L.N., Arch. Insect, Biochem. Physiol., 1985, vol. 2, p. 295.
Charoensuk, S., Yingyongnarongkul, B., and Suksamrarn, A., Tetrahedron, 2000, vol. 56, p. 9313.
Sarker, S.D., Sik, V., Rees, H.H., and Dinan, L., Phytochemistry, 1998, vol. 49, p. 2311.
Odinokov, V.N., Mendeleev Commun., 2005, vol. 15, p. 217.
Shereshovets, V.V., Khursan, S.L., Komissarov, V.D., and Tolstikov, G.A., Usp. Khim., 2001, vol. 70, p. 123.
Bailey, Ph.S. Chem. Rev., 1958, vol. 58, p. 925.
Greenwood, D.R., Dinan, L.N., and Rees, H.H., Biochem., 1984, vol. 217, p. 783.
Odinokov, V.N., Afon’kina, S.R., Shafikov, R.V., Savchenko, R.G., Galyautdinov, I.V., Khalilov, L.M., and Shashkov, A.S., Zh. Org. Khim., 2007, vol. 43, p. 830.
Odinokov, V.N., Nazmeeva, S.R., Savchenko, R.G., Galyautdinov, I.V., and Khalilov, L.M., Zh. Org. Khim., 2002, vol. 38, p. 550.
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Original Russian Text © R.G. Savchenko, Ya.R. Urazaeva, R.V. Shafikov, V.N. Odinokov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1163–1166.
For preliminary communication, see [1].
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Savchenko, R.G., Urazaeva, Y.R., Shafikov, R.V. et al. Regio and stereo directional oxidation of ecdysteroids and their 7,8-dihydroanalogs with ozone in pyridine. Russ J Org Chem 45, 1149–1153 (2009). https://doi.org/10.1134/S1070428009080065
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DOI: https://doi.org/10.1134/S1070428009080065