Advertisement

Transformed steroids

Communication 16. Wagner-Meerwein rearrangement of 16α, 17α-epoxypregn-5-ene-3β,20β-diol 3,20-diacetate under the conditions of the Grignard reaction
  • A. A. Akhrem
  • T. V. Ilyukhina
Organic and Biological Chemistry
  • 17 Downloads

Conclusions

  1. 1.

    The Wagner-Meerwein rearrangement of the starting oxide is observed when 16α,17α-epoxypregn-5-ene-3β,203-diol 3,20-diaeetate is reacted with methylmagnesium iodide.

     
  2. 2.

    The product of the indicated rearrangement is 18-nor-17β-methyl-17α-pregna-5,13 (14)-diene-3β, 16α,20β-triol.

     
  3. 3.

    It was discovered that the side chain of the steroidalβ-ketol is cleaved under alkaline conditions, which cleavage takes place by the retroaldol mechanism.

     

Keywords

Oxide Steroid Iodide Diol Alkaline Condition 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A.A. Akhrem and T.V. Ilyukhina, Izv. Akad. Nauk SSSR, Ser. Khim., 1574 (1968).Google Scholar
  2. 2.
    N.D. Hall and G. Just, Steroids,6, 111 (1965).Google Scholar
  3. 3.
    J.W. Blunt, J.M. Coxon, M.P. Hartshorn, and D.N. Kirk, Tetrahedron,23, 1811 (1967).Google Scholar
  4. 4.
    N.N. Suvorov, L.V. Sokolova, and N.V. Makarov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 2257 (1960).Google Scholar
  5. 5.
    B. Camerino and R. Modelli, Gazz. Chim. Ital.,86, 1219 (1956).Google Scholar
  6. 6.
    K. Bowden, I.M. Heilbron, E.R.H. Jones, and B.C.L. Weedon, J. Chem. Soc., 39 (1946).Google Scholar
  7. 7.
    K. Heusler and A. Wettstein, Ber.,87, 1301 (1954).Google Scholar
  8. 8.
    E. Kondo and T. Mitsugi, J. Am. Chem. Soc.,88, 4737 (1966).Google Scholar
  9. 9.
    C.A. Grob and P.W. Schiess, Angew. Chem.,79, 1 (1967).Google Scholar
  10. 10.
    C.G. Bergstrom, J. Med. Chem.,10, 440 (1967).Google Scholar
  11. 11.
    H.L. Herzog, O. Gnoj, L. Mandell, G.G. Nathansohn, and A. Vigevani, J. Org. Chem.,32, 2906 (1967).Google Scholar

Copyright information

© Consultants Bureau 1969

Authors and Affiliations

  • A. A. Akhrem
    • 1
  • T. V. Ilyukhina
    • 1
  1. 1.N.D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

Personalised recommendations