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

被引：4

作者：

Liang, Yu-Yan ^{[1
]}

Huang, Huan ^{[1
]}

Li, Yang ^{[1
]}

Du, Rong-Kai ^{[1
]}

Li, Jing ^{[1
]}

Liu, Yong-Hong ^{[2
]}

Li, Shan ^{[1
]}

Zhang, Lei ^{[1
]}

机构：

[1] South China Univ Technol, Sch Biol & Biol Engn, MOE Joint Int Res Lab Synthet Biol & Med, Guangzhou 510006, Peoples R China

[2] 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

来源：

STEROIDS | 2020年 / 157卷

关键词：

Chenodeoxycholic acid; Cholic acid; Hyodeoxycholic acid; Hydrogen inversion; omega-Muricholic; Selective oxidation; CHENODEOXYCHOLIC ACID; URSODEOXYCHOLIC ACID; STEREOCONTROLLED CONVERSION; BILE; ROUTE;

D O I：

10.1016/j.steroids.2020.108594

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

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.

引用

页数：8

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