Bile acids, LXXIX. Synthesis and reduction of 1,4-dien-3-ones of various bile acids.
1,4-Dien-3-ones of various bile acids (IIa-d), their methyl esters (IIe-h), and their formylated derivatives (IIi-k) were synthesized and their reduction investigated by both catalytic and chemical methods as an alternative route to the synthesis of allo bile acids. Lithium-ammonia reduction proved to be the better method for the reduction of these 1,4-dien-3-ones producing the 3-keto- and 3 beta-hydroxy-allo bile acids (Vb-d) and (VIb-d) in 66-72% yields.
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Edward A. Doisy Department of Biochemistry, St. Louis University School of Medicine, MO 63104.
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D000641:Ammonia; D001647:Bile Acids and Salts / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002770:Cholenes; D006865:Hydrogenation; D008094:Lithium; D010084:Oxidation-Reduction
D001647:Bile Acids and Salts; D002770:Cholenes; D000641:Ammonia; D008094:Lithium