Practical synthesis of chenodeoxycholic acid from phocaecholic acid.

He, Zengliang; Liang, Nengde; Zou, Sheng; Yu, Fang; Zeng, Yi; Chen, Xingjun; Wang, Yuanhua; Zhou, Li; Wang, Qiwei

He, Zengliang; Liang, Nengde; Zou, Sheng; Yu, Fang; Zeng, Yi; Chen, Xingjun; Wang, Yuanhua; Zhou, Li; Wang, Qiwei.

Affiliation

He Z; Department of Chemistry, Xihua University, Chengdu 610039, China; Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; University of Chinese Academy of Sciences, Beijing 100049, China.
Liang N; Department of Chemistry, Xihua University, Chengdu 610039, China.
Zou S; Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Yu F; Department of Chemistry, Xihua University, Chengdu 610039, China.
Zeng Y; Department of Chemistry, Xihua University, Chengdu 610039, China. Electronic address: zengy@mail.edu.cn.
Chen X; Department of Chemistry, Xihua University, Chengdu 610039, China.
Wang Y; College of Chemistry, Sichuan University, Chengdu 610041, China. Electronic address: yhwang@scu.edu.cn.
Zhou L; Center for Natural Products Research, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China. Electronic address: zhouli@cib.ac.cn.
Wang Q; Department of Chemistry, Xihua University, Chengdu 610039, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: wqw@cioc.ac.cn.

Steroids ; 209: 109470, 2024 Jul 10.

Article de En | MEDLINE | ID: mdl-38997080

ABSTRACT

ABSTRACT

In this study, we developed an effective method for the large-scale synthesis of chenodeoxycholic acid (CDCA) from phocaecholic acid (PhCA). A high total yield of up to 72 % was obtained via five steps including methyl esterification, Ts-protection, bromination, reduction, and hydrolysis. The structures of the intermediates were confirmed by 1H NMR (Nuclear Magnetic Resonance), 13C NMR, HRMS (High Resolution Mass Spectrometry), and IR (Infrared Spectroscopy) spectroscopies. This method offers a new and practical approach to the synthesizing of CDCA.

Mots clés

23-Hydroxyl group; Chenodeoxycholic acid; Phocaecholic acid; Steroid

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Texte intégral: 1 Collection: 01-internacional Base de données: MEDLINE Langue: En Journal: Steroids Année: 2024 Type de document: Article Pays d'affiliation: Chine