Controlled alkaline hydrolysis of 16-bromo-17-keto steroids without ketol rearrangement and its reaction mechanism

M Numazawa, Y Osawa

Index: Numazawa, Mitsuteru; Osawa, Yoshio Journal of the American Chemical Society, 1980 , vol. 102, # 16 p. 5402 - 5404

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Citation Number: 13

Abstract

Sir: on the relative stability of steroidal 16, l'I-ketols toward alkali hydroxide and the unsuccessful attempts to isolate thermodynamically unstable 16-hydroxy 17-ketone, it has been considered impossible to isolate the ketol by hydrolysis of 16-bromo 17-ketone. Two types of reactions of 16-bromo 17-ketone with other nucleophiles have been known, the direct displacement of bromine with amines3 and thi~ acetate,~ leading