Stereospecific synthesis of 16. alpha.-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism

M Numazawa, M Nagaoka…

Index: Numazawa, Mitsuteru; Nagaoka, Masao Journal of Organic Chemistry, 1982 , vol. 47, # 21 p. 4024 - 4029

Full Text: HTML

Citation Number: 78

Abstract

Synthesis of 16a-hydroxy-17-oxo steroids 3, 5b, and 6b and 3fi, 16a-dihydroxy-5-17- oxoandrosten-3-y1 sulfate (7) from 16a-bromo-17-oxo steroids 1, 5a, and 6a and the reaction mechanism of the controlled alkaline hydrolysis are described. Treatment of the bromo ketones with NaOH in aqueous DMF gave the 16a-hydroxy 17-ketones stereoselectively in 95% yield without formation of other ketols. The sodium salt of 3- ...