Abstract
CORTISONE acetate (IIb) has so far only been synthesized1 from bile acids which possess the ‘normal’ configuration at C-5 (rings A/B cis). Since the potentially most abundant sources, such as the steroidal sapogenins, belong to the allo series (rings A\B trans) or are readily convertible to the latter, it is important to accomplish the transformation of an allosteroid to cortisone. We have recently described2 a method for the conversion of 3-keto-allosteroids into δ4-3-ketones, which involved dibromination to a 2,4-dibromo derivative, treatment of the latter with sodium iodide in acetone solution to yield a 2-iodo-δ4-3-ketone and subsequent deiodination with chromous chloride, collidine or zinc. This procedure was applied successfully in the androstane, etioallocholanic acid and allopregnane series. The usefulness of this method for the important 17,21-dihydroxy-20-keto steroids remained to be demonstrated.
Similar content being viewed by others
Article PDF
References
Sarett, L. H., J. Biol. Chem., 162, 601 (1946); J. Amer. Chem. Soc., 70, 1454 (1948).
Rosenkranz, G., Djerassi, C., and co-workers, J. Amer. Chem. Soc., 72, 1046, 4077 (1950).
Fleisher, G., and Kendall, E. C., Abstracts, American Chemical Society, Atlantic City Meeting, September 1949, p. 15 M; J. Org. Chem., 16, 572 (1951).
Rosenkranz, G., Pataki, J., Kaufmann, St., Berlin, J., and Djerassi, C., J. Amer. Chem. Soc., 72, 4081 (1950).
Djerassi, C., and Scholz, C. R., J. Amer. Chem. Soc., 69, 2404 (1947); J. Org. Chem., 13, 697 (1948).
Julian, P. L., Meyer, E. W., Karpel, W. J., and Waller, I. R., J. Amer. Chem. Soc., 72, 5145 (1950). Koechlin, B. A., Kritchevsky, T. H., and Gallagher, T. F., ibid., 73, 189 (1951).
Stork, G., Romo, J., Rosenkranz, G., and Djerassi, C., J. Amer. Chem. Soc., 73 (July 1951). Rosenkranz, G., Pataki, J., and Djerassi, C., ibid. (in the press).
v. Euw, J., and Reichstein, T., Helv. Chim. Acta., 25, 1009 (1942).
The direct comparison is reported by Kaufmann, St., and Pataki, J., Experientia (in the press).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
ROSENKRANZ, G., DJERASSI, C., YASHIN, R. et al. Cortical Hormones from alloSteroids: Synthesis of Cortisone from Reichstein's Compound D. Nature 168, 28 (1951). https://doi.org/10.1038/168028a0
Issue Date:
DOI: https://doi.org/10.1038/168028a0
This article is cited by
-
Psychoimmunological effects of dioscorea in ovariectomized rats: role of anxiety level
Annals of General Psychiatry (2007)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.