Chemistry of C-16-Oxygenated 5α, 14β-Androstances

抄録

In connection with the studies on conformation of ring D of 5α, 14β-androstane, metal hydride reduction of 16-ketone and ring opening of 16β, 17β-epoxide with hydrogen bromide were examined. It was clarified that in 14β-series metal hydride would attack 16-oxo group from the less hindered β-side to yield 16α-hydroxy compound. The ring cleavage of 16β, 17β-epoxide with hydrogen bromide afforded 17α-bromo-16β-hydroxy derivative, which was readily acetylated in the presence of acetic acid and was converted again to the epoxide only by contact with alumina.