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 - Funding Information:
Funding: This research was supported by JSPS A3 Foresight Program (Asian Chemical Probe Research Hub), PRIME and the Platform Project for Supporting Drug Discovery and Life Science Research (BINDS) from the Japan Agency for Medical Research and Development, AMED, the JSPS KAKENHI (Grant Numbers 21K19053, 21H02070, and 20K15957), and Asian Chemical Biology Initiative. The APC was funded by the JSPS A3 Foresight Program.
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.
UR - http://www.scopus.com/inward/record.url?scp=85122003932&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85122003932&partnerID=8YFLogxK
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 -