Oxidation of 3β,5α6β-triacetoxycholestane using the Gif system (iron cluster–metallic zinc–pyridine–aqueous acetic acid) gives, as major product, the side-chain fission ketone 3β,5α,6β-triacetoxy-5α-pregnan-20-one. The 15- and 16-keto derivatives of the parent triacetate are also formed. Comparable results are obtained in the oxidation of cholestanol acetate and of acetoxycholestan-6-one ethylene ketal.
D. H. R. Barton, A. K. Göktürk, J. W. Morzycki and W. B. Motherwell, J. Chem. Soc., Perkin Trans. 1, 1985, 583 DOI: 10.1039/P19850000583
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