The Synthesis of Stero-Bile Acids

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Abstract
As a result of the comparative studies on the bile salt component in the bile of various vertebrates by Shimizu and co-workers, several kinds of stero-bile acids and bile-sterols were isolated from the bile of the animals of low class such as frog and toad. Formation of the stero-bile acids and bile-sterols in various vertebrates is of a considerable biogenetic interest, since these compounds might represent intermediate forms from the sterols to the normal bile acids. Shimizu, Oda and Kazuno (1, 2) isolated trihydroxybufosterocholenic acid (m. p. 160°) and trihydroxyisosterocholenic acid (m. p. 227°), having a probable formula of C28H46O59, from the bile of the toad (Bufo vulgaris formosus). S himizu and Kazuno (3, 4) classified later the nuclear structure and the location of the double bond of these acids, from the fact that both the isomeric acids were converted to bisnorcholic acid Various stero-bile acids have been syn~hesized in our laboratory in order to elucidate the chemical structure of the natural stero-bile acids (5), but the structure of trihydroxybufosterocholenic acid and trihydroxyisosterocholenic acid remained still unknown. The author, therefore, attempted to synthesize 3a, 7a, 12a-trihydroxy-24-methylcoprostanic acid which has the same structure as Shimizu and Kazuno (3, 4) suggested previously.

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