Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
2027645 | Steroids | 2015 | 7 Pages |
•Cross coupling of bile acids and 4-methoxycarbonyl phenylboronic was achieved.•24-(4′-Methoxycarbonylphenyl)-5β-cholan-24-ones were obtained.•Wolff–Kishner reduction of the obtained compounds led to new bile acids analogs.•X-ray and NMR allowed the unambiguous characterization.
Palladium-catalyzed cross coupling of 4-methoxycarbonyl phenyboronic acid with acetylated bile acids in which the carboxyl functions was activated by formation of a mixed anhydride with pivalic anhydride afforded the cross coupled compounds, which were converted in novel side chain modified bile acids by one pot carbonyl reduction/removal of the protecting acetyl groups by Wolff–Kishner reduction. Unambiguous assignments of the NMR signals and crystal characterization of the heretofore unknown compounds are provided.
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