Radical oxidation of 17-functionalized 14alpha-hydroxy steroids

V.A. Khripach, V.N. Zhabinskii, A.I. Kotyatkina, G.P. Fando, Y.Y. Zhiburtovich, A.S. Lyakhov, A.A. Govorova, M.B. Groen, J. van der Louw, A. de Groot

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11 Citations (Scopus)

Abstract

The radical oxidation of 14a-hydroxy steroids with various functional groups at C-17 was studied. Lead tetraacetate and ceric ammonium nitrate were used as oxidizing agents. It was shown that reactions of this type afforded complex mixtures of compounds. However, the radical oxidation of 14a-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85"ield. The structure and conformation of the formed 13a-iodo-3a,5-cyclo-13,14-seco-5a-androst-5-ene-14,17-dione was determined by X-ray analysis
Original languageEnglish
Pages (from-to)1764-1776
JournalCollection of Czechoslovak Chemical Communications
Volume66
DOIs
Publication statusPublished - 2001

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    Khripach, V. A., Zhabinskii, V. N., Kotyatkina, A. I., Fando, G. P., Zhiburtovich, Y. Y., Lyakhov, A. S., Govorova, A. A., Groen, M. B., van der Louw, J., & de Groot, A. (2001). Radical oxidation of 17-functionalized 14alpha-hydroxy steroids. Collection of Czechoslovak Chemical Communications, 66, 1764-1776. https://doi.org/10.1135/cccc20011764