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

  • Steroids. 2023 Jul:195:109227. doi: 10.1016/j.steroids.2023.109227.
Haiyun Zhao  1 ,  Zhicheng Zhong  1 ,  Maojie Chen  1 ,  Bin Sun  2 ,  Jiayang Wang  3 ,  Can Jin  4
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: [email protected].
  • 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: [email protected].
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 Δ5,25-3β-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.
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