Synthesis and Metabolism of Delta4-Cholestene-7alpha-ol-3-one. Bile Acids and Steroids 108.

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Abstract
A method of preparing [DELTA] 4-cholestene-7[alpha]-o1-3-one is described. This compound can be obtained in low yield (4[long dash]5%) from 3[beta]-benzoxy-7[alpha]-tetrahydro-2[image]-pyranyloxycholesterol by hydrolysis of the 3[beta]-benzoxy group. Oppenauer oxidation at this position followed by reduction with sodium borohydride yielding a 3-hydroxy-7-pyranyl ether with the double bond in the 4-position. Hydrolysis of this product followed by selective oxidation at the 3-position with MnO2 yielded [DELTA]4-cholestene-7[alpha]-o1-3-one. Randomly tritium-labelled [DELTA]4-cholestene-7[alpha]-ol-3-one, prepared biosynthetically by incubation of labelled 7[alpha]-hydroxycholesterol with mouse liver homogenates, has been administered to bile-fistula rats, and the labelled products in the bile have been separated with chromatography and partly identified. [DELTA]4 -Cholestene-7[alpha]-o1-3-one is metabolized in part to chenodeoxycholic acid and to cholic acid. In addition several unidentified bile acids of polarity similar to that of cholic as well as of chenodeoxycholic acid are formed.