Abstract
EARLY in 1948, I discussed by letter with Prof. L. F. Fieser the stereochemical course of reactions at, or adjacent to, C17 of the steroid nucleus. The experimental facts may be summarized as follows1. 
Steroids with normal configuration at C14 undergo reactions exemplified by A, B, C and D to afford largely or almost exclusively a single 17-epimeride in which the persisting extracyclic C17-valency bond is β-orientated: 
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References
Cf. Fieser, L. F., and Fieser, M., “Natural Products Related to Phenanthrene”, 410, 411 (3rd edit. New York: Reinhold, 1949).
Dostrovsky, Ingold and Hughes, J. Chem. Soc., 173 (1946).
Whitmore and Rothrock, J. Amer. Chem. Soc., 54, 343 (1932).
Quayle and Norton, J. Amer. Chem. Soc., 62, 1170 (1940).
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SHOPPEE, C. Stereochemical Course of Reactions at Steroid C17. Nature 166, 107–108 (1950). https://doi.org/10.1038/166107a0
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DOI: https://doi.org/10.1038/166107a0
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