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

被引：2

作者：

Fujii, Yui ^{[1
]}

Yoritate, Makoto ^{[1
]}

Makino, Kana ^{[1
]}

Igawa, Kazunobu ^{[2
]}

Takeda, Daiki ^{[1
]}

Doiuchi, Daiki ^{[3
]}

Tomooka, Katsuhiko ^{[2
]}

Uchida, Tatsuya ^{[3
]}

Hirai, Go ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, 3-1-1 Maidashi, Fukuoka, Fukuoka 8128582, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Integrated Res Consortium Chem Sci IRCCS, Kasuga, Fukuoka 8168580, Japan

[3] Kyushu Univ, Grad Sch Sci, Dept Chem, Nishi Ku, 744 Motooka, Fukuoka, Fukuoka 8190395, Japan

来源：

MOLECULES | 2022年 / 27卷 / 01期

关键词：

cholesterol; oxysterol; C-H oxidation; Ru (bpga); 25-hydroxycholesterol; dihydroxycholesterol; GENE-EXPRESSION; C-25;

D O I：

10.3390/molecules27010225

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：10

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