Transformed steroids

Communication 41. Reaction of 3-acetate of 16α, 17α-epoxy-δ5-pregnen-3/gb-ol-20-one with thiolacetic acid and synthesis of δ5-pregnene-3β,16/gb, 17α-triol-20-one 3-acetate, 16-thionoacetate
  • A. A. Akhrem
  • A. M. Turuta
  • E. P. Prokof'ev
Organic and Biological Chemistry
  • 16 Downloads

Conclusions

  1. 1.

    A method was developed for opening the oxide ring of the 3-acetate of 16α, 17α-epoxy-Δ5-pregnen-3β-ol-20-one with thiolacetic acid under ionic conditions.

     
  2. 2.

    The reaction proceeds with a predominant cleavage of the C16-O bond of the oxide ring and attack of the C16-center by the thiolacetic acid in the thiono form, with the formation of the 3-acetate, 16-thionoacetate of Δ5-pregnene-3β, 16β,17α-triol-20-one, the structure of which was assigned on the basis of the sum of the chemical and physicochemical methods.

     
  3. 3.

    A small amount (~ 6%) of the isomeric product of opening the ring is formed, which apparently arises as the result of the cleavage of the C17-O bond of the starting oxide by the thiol form of thiolacetic acid.

     

Keywords

Oxide Steroid Thiol Ionic Condition Physicochemical Method 

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Literature cited

  1. 1.
    A. A. Akhrem, A. M. Turuta, and E. P. Prokof'ev, Izv. Akad. Nauk SSSR, Ser. Khim., 2558 (1971).Google Scholar
  2. 2.
    A. A. Akhrem, V. A. Dubrovskii A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 2792 (1969).Google Scholar
  3. 3.
    K. Takeda, K. Kuriyama, and T. Komeno, Tetrahedron,21, 1203 (1965).Google Scholar
  4. 4.
    M. J. Janssen, Rec. Trav. Chim.,79, 464 (1960).Google Scholar
  5. 5.
    P. Reynaud and R. C. Moreau, Bull. Soc. Chim. France, 2999 (1964).Google Scholar
  6. 6.
    N. S. Bhacca and D. A. Williams, Application of NMR in Organic Chemistry [Russian translation], Mir, Moscow (1966).Google Scholar
  7. 7.
    A. Ohno, T. Koizumi, and G. Tsuchihashi, Tetrahedron Lett.,17, 2083 (1968).Google Scholar
  8. 8.
    P. Crabbé, Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, San Francisco-London-Amsterdam (1965).Google Scholar
  9. 9.
    P. Crabbé and F. McCapta, Tetrahedron,20, 2455 (1964).Google Scholar
  10. 10.
    A. A. Akhrem, Z. I. Istomina, G. A. Kogan, A. I. Kuznetsova, and A. M. Turuta, Izv. Akad. Nauk SSSR, Ser. Khim., 2503 (1969).Google Scholar
  11. 11.
    H. L. Herzog and O. Gnoi, J. Org. Chem.,32, 2906 (1967).Google Scholar
  12. 12.
    A. A. Akhrem, A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 416 (1972).Google Scholar
  13. 13.
    Establishing the Structure of Organic Compounds by Physical and Chemical Methods [in Russian], Vol. 1, Khimiya (1967).Google Scholar
  14. 14.
    A. A. Akhrem, G. A. Kogan, A. M. Turuta, I. S. Kovnatskaya, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 2100 (1971).Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • A. A. Akhrem
    • 1
  • A. M. Turuta
    • 1
  • E. P. Prokof'ev
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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