Steroids

Synthesis of hydroxylated steroid hormones via conjugate addition of a silyl-cuprate reagent

D Garside, DN Kirk, NM Waldron

Index: Garside, Diana; Kirk, David N.; Waldron, Norman M. Steroids, 1994 , vol. 59, # 12 p. 702 - 711

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Citation Number: 6

Abstract

Abstract The synthesis of several hydroxylated steroids via conjugate addition of Fleming's silyl-cuprate reagent (PhMe 2 Si) 2 CuLi, a masked hydroxyl group, to the appropriate enone was studied. By this means 7∝-hydroxytestosterone (7) was obtained in good yield from 17β-hydroxyandrosta-4, 6-dien-3-one (1a), though similar reactions of 17β-hydroxyandrosta- 1, 4-dien-3-one (8) gave a low yield of 1∝-hydroxytestosterone (13) chiefly through the ...