Journal of the American Chemical Society

“Enamine” Derivatives of Steroidal Carbonyl Compounds. III. The Synthesis of C11-Oxygenated Testosterones

ME Herr, FW Heyl

Index: Herr; Heyl Journal of the American Chemical Society, 1953 , vol. 75, p. 5927,5929

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Citation Number: 31

Abstract

lla-and 118-hydroxytestosterone have been prepared from 1 la-hydroxy-4-androstene-3, 17- dione and adrenosterone, respectively, by the formation of the Cr-enamine, reduction of the free carbonyl groups with lithium aluminum hydride and subsequent hydrolysis to regenerate the 3-keto-A '-system. 1 la-Hydroxytestosterone thus prepared was readily acylated at the Cl7-hydroxyl position and the resulting llp-hydroxy-17-ester upon oxidation ...