Pregnan-7-ol and Pregnan-12-ol

Abstract

Ruff and Reichstein1 have described a pregnan-7-ol and a pregnan-12-ol prepared by Wolff–Kishner reduction of acetoxypregnane ketones. They state that these two substances are probably the 7α- and 12α-hydroxy compounds; but since epimerization during Wolff–Kishner reduction is not excluded, they name them provisionally ‘7ξ’ and ‘12ξ’2. The molecular rotations of pregnan-7ξ-ol and of pregnan-12ξ-ol and their derivatives show that the two new compounds are indeed 7α and 12α.

References

  1. 1

    Ruff, A., and Reichstein, T., Helv. chim. Acta, 34, 70 (1951).

  2. 2

    The letter ‘ξ’ is used to indicate that the configuration of the substituent is unknown. Cf. “Proposals for Steroid Nomenclature” made by a conference at the CIBA Foundation, London. Chem. and Indust., p. SN1 (June 23, 1951).

  3. 3

    Barton, D. H. R., and Klyne, W., Chem. and Indust., 755 (1948).

  4. 4

    Barton, D. H. R., J. Chem. Soc., 813 (1945).

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KLYNE, W. Pregnan-7-ol and Pregnan-12-ol. Nature 168, 835 (1951). https://doi.org/10.1038/168835a0

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