AI Article Synopsis
- Five cholic acid derivatives were synthesized from hyodeoxycholic acid using selective oxidation techniques and stereocontrolled methods.
- Specific hydroxyl groups were introduced through hydrolysis or oxidation processes, leading to various derivatives.
- A successful synthetic route for CDCA with a yield of 45% was established, emphasizing good yields, stereoselectivity, and reproducibility in the production of these compounds.
Article Abstract
Five cholic acid derivatives (including allo-ω-muricholic acid and CDCA) were synthesized from hyodeoxycholic acid via selective oxidation of C3- or C6-hydroxyl groups by IBX and NBS oxidants and stereocontrolled conversion. The hydroxyl group could be introduced through hydrolyzing α-Br keto with KCO aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBHCN and ZnCl only at 5β configuration. A feasible synthetic route of CDCA from HDCA has been established to avoid the epimerization with the yield of 45% (8 steps). These strategies provided good yields, stereoselectivity and reproducibility for the preparation of cholic acid derivates and CDCA.
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| http://dx.doi.org/10.1016/j.steroids.2020.108594 | DOI Listing |
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