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  • Title: Improved synthesis of 5 beta-cholestan-26-oic acids.
    Author: Batta AK, Salen G, Tint GS, Shefer S.
    Journal: Steroids; 1979 May; 33(5):589-94. PubMed ID: 462499.
    Abstract:
    An improved method for the synthesis of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid and 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid is described. The method involves an Arndt-Eistert rearrangement of the corresponding diazoketone obtained by the action of diazoethane on 3 alpha, 7 alpha-diformyloxy-5 beta-cholane-24-carboxylic or 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholane-24-carboxylic acid chloride. The products are obtained in good yield and no isomeric 27-nor- 24-methyl acid contaminants are formed as encountered in the commonly employed Kolbe synthesis.
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