Russian Chemical Bulletin

, Volume 62, Issue 9, pp 2037–2040 | Cite as

Reaction of 5β,6β-epoxy-16α,17α-cyclohexapregnane with methylmagnesium iodide

  • I. S. Levina
  • L. E. Kulikova
  • V. V. Kachala
  • L. L. Khemchyan
Full Articles


On treatment with methylmagnesium iodide, 3β-acetoxy-5β,6β-epoxy-16α,17α-cyclo-hexapregnan-20-one undergoes 3-O-deacetylation along with the opening of the 5β,6β-epoxide ring to form 5α-methyl-6β-hydroxy steroid and the 6α-methyl-6β-hydroxy isomer, the 20-keto group remaining intact.

Key words

steroids epoxidation 16α,17α-cyclohexapregnanes methylmagnesium iodide 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    A. A. Akhrem, I. V. Ilukhina, Yu. A. Titov, Russ. Chem. Rev. (Engl. Transl.), 1969, 38, 850.CrossRefGoogle Scholar
  2. 2.
    S. Julia, C. Neuville, R. Kevorkian, C. R. Acad. Sci., 1964, 258, 5900.Google Scholar
  3. 3.
    A. V. Kamernitskii, I. S. Levina, Russ. J. Bioorg. Chem. (Engl. Transl.), 2005, 31, 105, 227 [Bioorg. Khim., 2005, 115, 227].Google Scholar
  4. 4.
    A. A. Akhrem, A. V. Kamernitskii, L. E. Kulikova, I. S. Levina, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 444 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1978, 27, 384].Google Scholar
  5. 5.
    S. L. H. Rebelo, M. M. Q. Simoes, M. Graca, P. M. S. Neves, A. M. S. Silva, J. A. S. Cavaleiro, A. F. Peixoto, M. M. Pereira, M. R. Silva, J. A. Paixao, A. M. Beja, Eur. J. Org. Chem., 2004, 4778.Google Scholar
  6. 6.
    J. F. S. Carvalho, M. Cruz Silva, M. L. Sae Melo, Tetrahedron, 2009, 65, 2773.CrossRefGoogle Scholar
  7. 7.
    P. A. Belyakov, V. I. Kadentsev, A. O. Chizhov, N. G. Kolotyrkina, A. S. Shashkov, V. P. Ananikov, Mendeleev Commun., 2010, 20, 125.CrossRefGoogle Scholar
  8. 8.
    A. A. Akhrem, L. E. Kulikova, I. S. Levina, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1972, 21 1308 [Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 1308].CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • I. S. Levina
    • 1
  • L. E. Kulikova
    • 1
  • V. V. Kachala
    • 1
  • L. L. Khemchyan
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations