TY - JOUR
T1 - Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst
AU - Fujii, Yui
AU - Yoritate, Makoto
AU - Makino, Kana
AU - Igawa, Kazunobu
AU - Takeda, Daiki
AU - Doiuchi, Daiki
AU - Tomooka, Katsuhiko
AU - Uchida, Tatsuya
AU - Hirai, Go
N1 - Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2022/1/1
Y1 - 2022/1/1
N2 - 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.
AB - 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.
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U2 - 10.3390/molecules27010225
DO - 10.3390/molecules27010225
M3 - Article
C2 - 35011456
AN - SCOPUS:85122003932
SN - 1420-3049
VL - 27
JO - Molecules
JF - Molecules
IS - 1
M1 - 225
ER -