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Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer

Authors
Journal
Steroids
0039-128X
Publisher
Elsevier
Publication Date
Volume
28
Issue
5
Identifiers
DOI: 10.1016/0039-128x(76)90007-6

Abstract

Abstract To aid in the identification of trihydroxy acidic metabolite(s) derived from β-sitosterol, 3α,7α,12α-trihydroxy-24-nor-5β-cholan-3oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7α,12α-dihydroxy-24-nor-5α-cholanate, 3-oxo-7α,12α-dihydroxy-24-nor-5β-cholanate and 3-oxo-7α,12α-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5β-derivative with SeO 2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and other physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.

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