Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis of 15β, 16β-methyleneprogesterone

  • 27 Accesses

Abstract

15β,16β-Methyleneprogesterone was produced from 15β,16β-methylene-3β-hydroxyandrost-5-en-17-one with Wittig olefination of 17-ketone by methoxymethylenetriphenylphosphorane as the key stage.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    G.Teutsch, inAdrenal Steroid Antagonism, Eds.M.K.Agarwal and W.de Gruyter, Berlin, 1984, p.43.

  2. 2.

    F.J.Zeelen,Trends Pharmacol.Sci., 1983,4, 520.

  3. 3.

    D.H.Seeley, W.-Y.Wang, and H.A.Salganick,J.Biol.Chem., 1982,257, 13359.

  4. 4.

    A.V.Kamernitzky and I.S.Levina,Khim.-Farm.Zh., 1991,25, 4. [Pharm.Chem.J., 1991].

  5. 5.

    A.V.Kamernitzky, I.S.Levina, L.E.Kulikova, V.V.Korkhov, G.V.Nikitina, and M.Bol',Bioorgan.Khim., 1988,14, 828 [Sov.J.Bioorgan.Chem., 1988].

  6. 6.

    A.V.Kamernitzky, T.N.Galakhova, I.S.Levina, B.S.El'yanov, V.S.Bogdanov, and E.G.Cherepanova,Izv.Akad.Nauk SSSR. Ser.Khim., 1985, 1893 [Bull.Acad.Sci.USSR. Div.Chem.Sci., 1985,34, 1743].

  7. 7.

    D.M.Pistak and J.Wisha,Chem.Revs., 1978,78, 199.

  8. 8.

    Ch.-YonByon and M.Gut,J.Org.Chem., 1980,45, 4404.

  9. 9.

    N.R.Schmuff and B.M.Trost,J.Org.Chem., 1983,48, 1404.

  10. 10.

    G.Schubert, B.Schonecker, M.Wunderwald, and K.Ponsold,Pharmazie,41, 469.

  11. 11.

    R.H.Peters, D.F.Crowe, M.A.Avery, W.K.M.Chong, and M.Tanabe,J.Med.Chem., 1989,32, 1642.

  12. 12.

    R.Coulson,Tetrahedron Lett., 1964, 3323.

  13. 13.

    A.F.Kluge and I.S.Cloudsdale,J.Org.Chem., 1979,44, 4847.

  14. 14.

    W.G.Dauben and J.J.Taksugi,Tetrahedron Lett., 1987,28, 4377.

  15. 15.

    N.L.Isaacs and G.N.El-Din,Tetrahedron Lett., 1987,28, 2191.

  16. 16.

    T.A.Zhidkova, G.A.Stashina, A.R.Bekker, L.A.Vakulova, V.M.Zhulin, and G.I.Samokhvalov,Zh.Org.Khim., 1984,20, 2558 [J.Org.Chem.USSR, 1984].

  17. 17.

    T.N.Galakhova, G.A.Stashina, V.M.Zhulin, A.V.Kamernitsky and I.S.Levina,Izv.Akad.Nauk SSSR. Ser.Khim., 1990, 2877 [Bull.Acad.Sci. USSR. Div.Chem.Sci., 1990,39, 2613].

  18. 18.

    O.Schmidt, K.Prezewowsky, G.Schulz, and R.Wiechert,Chem.Ber., 1968,101, 939.

  19. 19.

    R.Wiechert, D.Bittler, and G.-A.Hoyer,Chem.Ber., 1973,106, 888.

  20. 20.

    J.W.Blunt and J.B.Stothers,Org.Magn.Reson., 1977,9, 439.

Download references

Author information

Additional information

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 203–207, January, 1993.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Galakhova, T.N., Levina, I.S., Kamernitzky, A.V. et al. Synthesis of 15β, 16β-methyleneprogesterone. Russ Chem Bull 42, 185–188 (1993). https://doi.org/10.1007/BF00700006

Download citation

Key words

  • Wittig reaction
  • olefination
  • androstane
  • pregnane
  • progesterone