Oxygenation of the 14α-methyl group in 3β-acetoxy-7α-hydroxy-14α-methyl-5α-cholestane has been achieved by reaction with lead tetra-acetate. Cleavage of the resulting 7α,32-epoxide with pyridine hydrochloride in refluxing acetic anhydride gave 3β-acetoxy-14α-acetoxymethyl-5α-cholest-7-ene, while chromium trioxide in acetic acid afforded the lactol derived from 3β-acetoxy-7-oxo-5α-cholestane-14α-carboxylic acid.
J. C. Knight, J. L. Belletire and G. R. Pettit, J. Chem. Soc. C, 1967, 2427 DOI: 10.1039/J39670002427
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