A novel synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one

Abstract

Jones oxidation of 5α-cholesta-8,14-dien-3β-yl acetate furnishes 9α-hydroxy-15-oxo-5α-cholest-8(14)-en-3β-yl acetate (4a). Treatment of (4a) with zinc dust and sulphuric acid followed by saponification gives 3β-hydroxy-5α-cholest-8(14)-en-15-one. On the basis of chemical and spectroscopic evidence, the product obtained by oxidation of 5α-cholest-8,14-dien-3β olis formulated as 9α-hydroxy-5α-cholest-8(14)-ene-3,15-dione (4b) and not as 14α-hydroxy-5α-cholest-8-ene-3,7-dione (3) as reported by others.