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Abstract
The synthesis of several hydroxylated steroids via conjugate addition of Fleming's silyl-cuprate reagent (PhMe 2Si) 2CuLi, 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 poor conversion of the phenylsilyl intermediate into the halogenosilane. 3β,16∝-Dihydroxy-5∝-pregnan-20-one ( 18b ) was obtained in a similar manner from 3β-hydroxy-5∝-pregn-16-en-20-one and 5∝-cholestane-1∝,3∝-diol ( 17 ) was produced from the 1-en-3-one ( 14 ) via conjugate addition of the silyl group, reduction of the carbonyl function, and oxidative removal of the silyl group.
Published Version
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