Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst

Yui Fujii, Makoto Yoritate, Kana Makino, Kazunobu Igawa, Daiki Takeda, Daiki Doiuchi, Katsuhiko Tomooka, Tatsuya Uchida, Go Hirai

Research output: Contribution to journalArticlepeer-review

Abstract

Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

Original languageEnglish
Article number225
JournalMolecules
Volume27
Issue number1
DOIs
Publication statusPublished - Jan 1 2022

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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