Preparation of Oxysterols by C-H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst

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) (PPh )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)- -(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpg...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 1; p. 225
Main Authors Fujii, Yui, Yoritate, Makoto, Makino, Kana, Igawa, Kazunobu, Takeda, Daiki, Doiuchi, Daiki, Tomooka, Katsuhiko, Uchida, Tatsuya, Hirai, Go
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 30.12.2021
MDPI
Subjects
25-hydroxycholesterol
Acids
Biosynthesis
Catalysts
Cholesterol
Chromatography
Communication
C–H oxidation
dihydroxycholesterol
High performance liquid chromatography
Liquid chromatography
Metabolites
Oxidation
oxysterol
Ru (bpga)
Selectivity
25-hydroxycholesterol
Ru (bpga)
oxysterol
cholesterol
dihydroxycholesterol
C–H oxidation
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Summary: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) (PPh )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)- -(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.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27010225