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Ein neues Verfahren zur Herstellung von 19-Norsteroiden

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Summary

The new methods for the production of 19-norsteroids described involve the conversion of 5α-halogen-6β-hydroxy-steroids into the corresponding 5α-halogen-6β:19-ethers either with lead tetraacetate or by the hypoiodite reaction8,10. The 6β:19-oxygen bridge is then opened reductively either directly or after oxidation of the 6β:19-ethers to lactones or preferably after introduction of a Δ4,6-3-oxo grouping. Acylolytic cleavage of the Δ4-3-oxo-6β:19-ethers followed by alkaline hydrolysis gives Δ4,6-3-oxo-19-hydroxy-steroids. The 19-hydroxycompounds formed are easily converted into 19-norsteroids by known methods.

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Authors and Affiliations

  1. Pharmazeutische Abteilung, Forschungslaboratorien der CIBA Aktiengesellschaft, Basel, Schweiz

    K. Heusler, J. Kalvoda, Ch. Meystre, H. Ueberwasser, P. Wieland, G. Anner & A. Wettstein

Authors
  1. K. Heusler
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  2. J. Kalvoda
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  3. Ch. Meystre
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  4. H. Ueberwasser
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  5. P. Wieland
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  6. G. Anner
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  7. A. Wettstein
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Additional information

Über Steroide, 189. (vorläufige) Mitteilung; 188. Mitt. vgl.J. Kalvoda, J. Schmidlin, G. Anner undA. Wettstein, Exper.18, 398 (1962).

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Heusler, K., Kalvoda, J., Meystre, C. et al. Ein neues Verfahren zur Herstellung von 19-Norsteroiden. Experientia 18, 464–466 (1962). https://doi.org/10.1007/BF02175863

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  • DOI: https://doi.org/10.1007/BF02175863

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