Investigation on the synthesis of 24-(R)-hydroxycholesterol

Haiyun Zhao; Zhicheng Zhong; Maojie Chen; Bin Sun; Jiayang Wang; Can Jin

doi:10.1016/j.steroids.2023.109227

Investigation on the synthesis of 24-(R)-hydroxycholesterol

Steroids. 2023 Jul:195:109227. doi: 10.1016/j.steroids.2023.109227. Epub 2023 Mar 24.

Authors

Haiyun Zhao¹, Zhicheng Zhong¹, Maojie Chen¹, Bin Sun², Jiayang Wang³, Can Jin⁴

Affiliations

¹ College of Pharmaceutical Sciences, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, PR China.
² College of Pharmaceutical Sciences, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, PR China; Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, Hangzhou 310014, PR China. Electronic address: sunbin@zjut.edu.cn.
³ School of Life Sciences, Huzhou University, Huzhou, Zhejiang, PR China.
⁴ College of Pharmaceutical Sciences, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, PR China; Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, Hangzhou 310014, PR China. Electronic address: jincan@zjut.edu.cn.

PMID: 36966967
DOI: 10.1016/j.steroids.2023.109227

Abstract

A facile and novel strategy has been developed for synthesis of 24-(R)-hydroxycholesterol, a key intermediate of tacalcitol, starting from 24-dehydrocholesterol in seven steps with 48.2% overall yield and high diastereomer ratio. Photocatalytic oxidation of olefins by employing inexpensive Rose Bengal as photosensitizer and air as the sole oxidant for the preparation of Δ^5,25-3β-Hydroxycholestadiene-24-one-3-acetate is the key step in this synthetic route. This developed strategy features mild conditions, satisfied total yield and excellent stereoselectivity (24-R/S = 97.7:2.3), providing a novel access to the 24-(R)-hydroxycholesterol.

Keywords: Asymmetric reduction; Desmosterol; Photo-catalytic; Tacalcitol.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes
Desmosterol*
Hydroxycholesterols*
Oxidation-Reduction

Substances

Hydroxycholesterols
Desmosterol
Alkenes