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

Molecules. 2021 Dec 30;27(1):225. doi: 10.3390/molecules27010225.

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.

PMID:35011456 | PMC:PMC8746986 | DOI:10.3390/molecules27010225

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