Preparation of Oxysterols by C-H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst.
Yui FujiiMakoto YoritateKana MakinoKazunobu IgawaDaiki TakedaDaiki DoiuchiKatsuhiko TomookaTatsuya UchidaGo HiraiPublished in: Molecules (Basel, Switzerland) (2021)
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 3 )] 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.
Keyphrases
- high performance liquid chromatography
- visible light
- ionic liquid
- energy transfer
- hydrogen peroxide
- room temperature
- tandem mass spectrometry
- electron transfer
- mass spectrometry
- highly efficient
- simultaneous determination
- solid phase extraction
- reduced graphene oxide
- ms ms
- carbon dioxide
- metal organic framework
- gold nanoparticles
- nitric oxide
- high resolution
- liquid chromatography
- crystal structure