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Isomerization of 14-hydroxy-17-ketosteroids: New examples of two-centered inversion of the C/D ring fusion and X-ray diffraction structural analysis of d,ℓ-3-methoxy-14β-hydroxy-8β, 9α-estra-1,3,5(10)-trien-17-one

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

d,ℓ-3-Methoxy-14β-hydroxy-8α,9β-estra-1,3,5(10)-trien-17-one (I) undergoes two-centered isomerization in alkaline medium to d,ℓ-3-methoxy-14β-hydroxy-8β,9α-estra-1, 3,5(10)-trien-17-one (II) in 70% yield. Under analogous conditions, natural isomer (II) is converted into synthetic isomer (I) in 20% yield. The crystalline and molecular structure of isomer (II) was established.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR, Moscow

    M. Kh. Dzhafarov, S. V. Lindeman, Yu. T. Struchkov, S. Kh. Karamyan & S. N. Ananchenko

  2. M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow

    M. Kh. Dzhafarov, S. V. Lindeman, Yu. T. Struchkov, S. Kh. Karamyan & S. N. Ananchenko

Authors
  1. M. Kh. Dzhafarov
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  2. S. V. Lindeman
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  3. Yu. T. Struchkov
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  4. S. Kh. Karamyan
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  5. S. N. Ananchenko
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2878–2883, December, 1991.

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Dzhafarov, M.K., Lindeman, S.V., Struchkov, Y.T. et al. Isomerization of 14-hydroxy-17-ketosteroids: New examples of two-centered inversion of the C/D ring fusion and X-ray diffraction structural analysis of d,ℓ-3-methoxy-14β-hydroxy-8β, 9α-estra-1,3,5(10)-trien-17-one. Russ Chem Bull 40, 2511–2515 (1991). https://doi.org/10.1007/BF00959735

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  • DOI: https://doi.org/10.1007/BF00959735

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