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Transformed steroids

Communication 31. Synthesis of model 20α, 21- and 20β, 21-diacetates of Δ4-isopregnene-17β,20ξ,21-triol-3-ones in order to establish the configuration of the C-20 epimeric Δ4-isopregnene-17β,20ξ-diol-3-on-21-oic acids


  1. 1.

    A method was developed for the synthesis of the difficultly accessible, epimeric at the 20-earbon center, 20α,21- and 20β,21-diacetates of the Δ4-isopregnene-17β,20ξ,21-triol-3-ones.

  2. 2.

    Conditions were selected for the preparative separation of the C-20 epimeric acetonides of A5-isopregnene-3β, 17β,20ξ,21-tetrol, and also of the acetonides of Δ-isopregnene-17β,20ξ,21-triol-3-one.

  3. 3.

    The structure of all of the synthesized compounds was confirmed by chemical and physical methods.

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Literature cited

  1. 1.

    A. A. Akhrem and T. K. Ustynyuk, Izv. Akad. Nauk SSSR, Ser. Khim., 2331 (1967).

  2. 2.

    H. Reich, C. Montigel, and T. Reichstein, Helv. Chim. Aeta,24, 977 (1941).

  3. 3.

    I. Salamon and T. Reichstein, Helv. Chim. Acta, 30, 1929 (1947).

  4. 4.

    L. F. Fieser and M. Fieser, Experientia,4, 285 (1948).

  5. 5.

    W. Klyne and D. H. R. Barton, J. Am. Chem. Soc.,71, 1500 (1949).

  6. 6.

    L. Ruzicka, K. Hofmann, and H. F. Meldahl, Helv. Chim. Acta,21, 597 (1938).

  7. 7.

    L. Ruzicka and P. Müller, Helv. Chim. Acta,22, 755 (1939).

  8. 8.

    J. S. Baran, J. Org. Chem.,25, 257 (1960).

  9. 9.

    A. A. Akhrem and A. I. Kuznetsova, Thin-Layer Chromatography [in Russian], Nauka (1964).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 136–141, January, 1971.

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Akhrem, A.A., Ustynyuk, T.K. Transformed steroids. Russ Chem Bull 20, 115–119 (1971).

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  • Steroid
  • Diacetates
  • Physical Method
  • Acetonides
  • Preparative Separation