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

Mario Anastasia,  Alberto Fiecchi  and  Antonio Scala 

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.

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Article type: Paper
DOI: 10.1039/P19790001821
Citation: J. Chem. Soc., Perkin Trans. 1, 1979,0, 1821-1824
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    A novel synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one

    M. Anastasia, A. Fiecchi and A. Scala, J. Chem. Soc., Perkin Trans. 1, 1979, 0, 1821
    DOI: 10.1039/P19790001821

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