Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid.

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 K2CO3 aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBH3CN and ZnCl2 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. Copyright © 2020 Elsevier Inc. All rights reserved.

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Yu-Yan Liang, Huan Huang, Yang Li, Rong-Kai Du, Jing Li, Yong-Hong Liu, Shan Li, Lei Zhang. Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid. Steroids. 2020 May;157:108594

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PMID: 32068077

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