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Synthesis and Dehydrohalogenation of 3 β-Chloro-5 α,7 α-dibromo-6-ketosteroids of the Stigmastane and Cholestane Series

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Abstract

3β-Chloro-5α,7α-dibromo-6-ketosteroids 5a and 5b are synthesized from β-sitosterol (1a) and cholesterol (1b). Dehydrohalogenation of these forms 7α-bromo-2,4-dien-6-ones (6a-b), 2,4-dien-6-ones (7a-b), and 14α-hydroperoxy-2,4,7-trien-6-ones (8a-b). Woodward hydroxylation of dienone 6a produces 2β-iodo-7α-bromo-3α-acetoxy-Δ4-6-ketone 9 and 7α-bromo-2α,3α-diacetoxy-Δ4-6-ketone 10. 2β-Iodo-3α-acetoxy-Δ4,7,14-trien-6-one 11 is prepared analogously from trienone 8a.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141, Belarus, Minsk, ul. Akad. Kuprevicha, 5/2

    N. V. Kovganko & V. L. Survilo

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  1. N. V. Kovganko
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  2. V. L. Survilo
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Kovganko, N.V., Survilo, V.L. Synthesis and Dehydrohalogenation of 3 β-Chloro-5 α,7 α-dibromo-6-ketosteroids of the Stigmastane and Cholestane Series. Chemistry of Natural Compounds 38, 257–263 (2002). https://doi.org/10.1023/A:1020432027888

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