Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid
文献类型：期刊论文
| 作者 | Liang, Yu-Yan; Huang, Huan; Li, Yang; Du, Rong-Kai; Li, Jing; Liu, Yong-Hong; Li, Shan; Zhang, Lei6 |
| 刊名 | STEROIDS
 |
| 出版日期 | 2020 |
| 卷号 | 157页码:108594 |
| 关键词 | Chenodeoxycholic acid Cholic acid Hyodeoxycholic acid Hydrogen inversion omega-Muricholic Selective oxidation |
| ISSN号 | 0039-128X |
| DOI | 10.1016/j.steroids.2020.108594 |
| 英文摘要 | Five cholic acid derivatives (including allo-omega-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 alpha-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 5 beta 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. |
| 资助机构 | National Major Scientific and Technological Special Project for Significant New Drugs Development [2018ZX09201002]; Foundation of Guangdong Provincial Department of Science and Technology [2016A010121004] ; National Major Scientific and Technological Special Project for Significant New Drugs Development [2018ZX09201002]; Foundation of Guangdong Provincial Department of Science and Technology [2016A010121004] |
| 源URL | [http://ir.scsio.ac.cn/handle/344004/18437]  |
| 专题 | 南海海洋研究所_中科院海洋生物资源可持续利用重点实验室 |
| 作者单位 | 1.[Liang, Yu-Yan 2.Huang, Huan 3.Li, Yang 4.Du, Rong-Kai 5.Li, Jing 6.Li, Shan 7.South China Univ Technol, Sch Biol & Biol Engn, MOE Joint Int Res Lab Synthet Biol & Med, Guangzhou 510006, Peoples R China 8.Chinese Acad Sci, South China Sea Inst Oceanol, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, Guangzhou 510301, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liang, Yu-Yan,Huang, Huan,Li, Yang,et al. Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid[J]. STEROIDS,2020,157:108594. |
| APA | Liang, Yu-Yan.,Huang, Huan.,Li, Yang.,Du, Rong-Kai.,Li, Jing.,...&Zhang, Lei.(2020).Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid.STEROIDS,157,108594. |
| MLA | Liang, Yu-Yan,et al."Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid".STEROIDS 157(2020):108594. |
入库方式： OAI收割
来源：南海海洋研究所
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