Abstract
The epoxidation of the diterpene hydrocarbon cembrene with peracetic acid in methylene chloride in the presence of sodium bicarbonate forms a single triepoxide — 4,5:7,8:11,12-triepoxycembrene with the 4S, 5R, 7S, 8S, 11S, 12S configuration of the asymmetric centers. The structure and stereochemistry of triepoxycembrene have been determined with the aid of x-ray structural analysis.
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V. A. Raldugin, L. Ya. Korotkikh, A. I. Rezvukhin, and V. A. Pentegova, Khim. Prir. Soedin., 525 (1977).
Yu. V. Gatilov and Zh. V. Dubovenko, Zh. Strukt. Khim.,20, 319 (1979).
M. G. B. Drew, D. H. Templeton, and A. Zalkin, Acta Crystallogr.,B25, 261 (1969).
F. P. Greenspan, J. Am. Chem. Soc.,68, 907 (1946).
Additional information
Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 174–178, March–April, 1981.
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Raldugin, V.A., Yaroshenko, N.I. & Gatilov, Y.V. Stereoselectivity of the exhaustive epoxidation of cembrene by peracetic acid. Crystalline and molecular structure of triepoxycembrene. Chem Nat Compd 17, 133–136 (1981). https://doi.org/10.1007/BF00634729
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DOI: https://doi.org/10.1007/BF00634729