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. 
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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).
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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
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DOI: https://doi.org/10.1038/168028a0
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