Tetrahedron p. 851 - 854 (1984)
Update date:2022-08-28
Topics:
Tal, Daniel M.
Frisch, G. Douglas
Elliott, William H.
The K-Selectride reduction at low temperature (-45 C) of 7-oxo-5α-cholestan-3β-yl acetate and methyl 7-oxo-3α-hydroxy-5β-cholanoate resulted in almost quantitative yield of the 7α-alcohol in the 5α-compound but only moderate yield of the 5β-analog.The simultaneous reduction of two carbonyl in the 3 and 7 positions afforded good to excellent yields of the diaxial diol in planar steroids (methyl 3,7-dioxo-5α-cholanoate, 3,7-dioxo-5α-cholestane and methyl 3,7-dioxo-5α-cholestan-27-oate) and only 14percent of 3α,7α-(OH)2 from methyl 3,7-dioxo-5β-cholanoate.
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