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Zur Umsetzung von 3α-Hydroxy-5β-Steroiden mit Blei(IV)-acetat

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Summary

On treatment of 3α-hydroxy-5β-steroids with lead tetra-acetate formation of 3α, 9α-oxides is observed. The yields of this ring closure reaction decrease significantly in the order 11-keto, Δ9, 11-ene and ring-C saturated compounds.

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References

  1. G. Cainelli, M. Lj. Mihailović, D. Arigoni undO. Jeger, Helv. chim. Acta42, 1124 (1959).

    Article  CAS  Google Scholar 

  2. Vgl. fernerK. Heusler, J. Kalvoda, Ch. Meystre, P. Wieland, G. Anner, A. Wettstein, G. Cainelli, D. Arigoni undO. Jeger, Exper.16, 21 (1960).

    CAS  Google Scholar 

  3. L. Velluz, G. Muller, R. Bardoneschi undA. Poittevin, C. R. Acad. Sci.250, 725 (1960).

    CAS  Google Scholar 

  4. A. Bowers, L. C. Ibáñez, M. Elena Cabezas undH. J. Ringold, Chem. & Ind.1960, 1299.

  5. G. Rosenkranz, J. Pataki undC. Djerassi, J. org. Chem.17, 290 (1952).

    Article  CAS  Google Scholar 

  6. V. R. Mattox, R. B. Turner, W. F. McGuckin, E. J. H. Chu undE. C. Kendall, J. Amer. chem. Soc.74, 5818 (1952).

    Article  CAS  Google Scholar 

  7. Nach Abschluss dieser Arbeit haben wir in einer Privatmitteilung von Dr.A. Bowers (vgl. auchA. Bowers undE. Denot, J. Amer. chem. Soc.82, 4956 (1960) von Umsetzungen von (20R)-3α, 20-Dihydroxy-11-keto-5β-pregnan und von (20R)-3α, 11β, 20-Trihydroxy-5β-pregnan mit Blei(IV)-acetat erfahren, die in 5-, bzw. 2,7proz. Ausbeute die Isolierung von (20R)-3α, 9α-Oxido-11-keto-20-hydroxy-5β-pregnan ermöglichten. Im letzteren Fall geht der 3α, 9α-Ätherring-Bildung wohl die Oxydation der 11β-Hydroxy-zur il-Keto-Gruppe voraus.

    Article  CAS  Google Scholar 

  8. E. P. Oliveto, T. Clayton undE. B. Hershberg, J. Amer. chem. Soc.75, 486 (1953).

    Article  CAS  Google Scholar 

  9. R. Criegee, Angew. Chemie70, 173 (1958).

    Article  CAS  Google Scholar 

  10. R. Criegee, L. Kraft undB. Rank, Liebigs Ann.507, 159 (1933).

    Article  CAS  Google Scholar 

  11. K. Heusler et al. (s. unter1).

  12. E. Elisberg, H. Vanderhaeghe, T. F. Gallagher, J. Amer. chem. Soc.74, 2814 (1952).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Organisch-chemisches Laboratorium der Eidgenössischen Technischen Hochschule, Zürich

    H. Immer, M. Lj. Mihailović, K. Schaffner, D. Arigoni & O. Jeger

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  1. H. Immer
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  2. M. Lj. Mihailović
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  3. K. Schaffner
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  4. D. Arigoni
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  5. O. Jeger
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Immer, H., Mihailović, M.L., Schaffner, K. et al. Zur Umsetzung von 3α-Hydroxy-5β-Steroiden mit Blei(IV)-acetat. Experientia 16, 530–532 (1960). https://doi.org/10.1007/BF02158436

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