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Bile acids. LXXI. A new synthesis of (25R)-3α, 7α-dihydroxy-[5α,6α-3H2]-5α-cholestan-26-oic acid (1)

✍ Scribed by Daniel M. Tal (2); William H. Elliott; Edward A. Doisy

Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
313 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Tritiation of 7‐oxo‐5‐cholestene‐3β,26‐diol diacetate afforded a mixture of [5α,6α‐^3^H~2~] products which were reduced with lithium aluminum hydride to provide a mixture of [5α,6α‐^3^H~2~]‐3β, (7α and 7β), 26‐triols an 3β, 26‐diol. Oxidation with Jones reagent provided 3,7‐dioxo and 3‐oxo‐[5α,6α‐^3^H~2~]‐5α‐cholestanoic acids which were separated. Stereospecific reduction of the 3,7‐dioxo methyl ester with K‐Selectride followed by alkaline hydrolysis afforded (25R)‐3α,7α‐dihydroxy‐[5α,6α‐^3^H~2~]‐5α‐cholestan‐26 ‐oic acid.

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