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Autooxidation of Δ17(20)-20-hydroxy derivatives of steroids. Synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one and its reduction to 17α-hydroxy derivative

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Abstract

An efficient procedure was proposed for the synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one. Optimal conditions were found for the combined process including 1,4-addition of methylmagnesium bromide at the Δ16-20-oxo fragment of dehydropregnenolone acetate and autooxidation of resulting bromomagnesium 3β-acetoxy-16α-methylpregna-5,17(20)-dien-20-olate. The subsequent reduction of the 17α-hydroperoxy group and hydrolysis of the 3β-acetoxy group afforded 17α-hydroxy-16α-methyl-substituted dehydropregnenolone acetate and its 3-hydroxy analog in high yield.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    T. S. Savinova, N. V. Lukashev & I. P. Beletskaya

  2. Institute of Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet. Cau Giay, Hanoi, Vietnam

    L. D. Huy

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  1. T. S. Savinova
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  2. N. V. Lukashev
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  3. L. D. Huy
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  4. I. P. Beletskaya
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Correspondence to T. S. Savinova.

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Original Russian Text © T.S. Savinova, N.V. Lukashev, L.D. Huy, I.P. Beletskaya, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 57–64.

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Savinova, T.S., Lukashev, N.V., Huy, L.D. et al. Autooxidation of Δ17(20)-20-hydroxy derivatives of steroids. Synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one and its reduction to 17α-hydroxy derivative. Russ J Org Chem 47, 54–61 (2011). https://doi.org/10.1134/S1070428011010052

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  • DOI: https://doi.org/10.1134/S1070428011010052

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