Dehydration of Bile Acids and their Derivatives. IX. Oxidation of Methyl 3α-Acetoxy-Δ7-cholenate with Selenium Dioxide

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Carefully repeated experiments have shown that, contrary to Fieser's report3), methyl 3α-acetoxy-Δ7-cholenate and some other un-saturated bile acids (5β) listed in Table I give positive results in the selenium dioxide test. This finding was substantiated by the fact that two oxidation products of methyl 3α-acetoxy-Δ7-cholenate were isolated, one of which was proved to be methyl 3α-acetoxy-7ξ, 15ξ-dihydroxy-Δ8(14)-cholenate. It is very interesting to note that, unlike the Δ7-steroids of the 5α-series, not only C7-H, but C15-H of the unsaturated bile acid mentioned above was oxidized with selenium dioxide to give hydroxyl groups, both of which remained without being acetylated under the experimental conditions described.
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