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

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(B...

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Autores principales: Fujii, Yui, Yoritate, Makoto, Makino, Kana, Igawa, Kazunobu, Takeda, Daiki, Doiuchi, Daiki, Tomooka, Katsuhiko, Uchida, Tatsuya, Hirai, Go
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8746986/
https://www.ncbi.nlm.nih.gov/pubmed/35011456
http://dx.doi.org/10.3390/molecules27010225
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author Fujii, Yui
Yoritate, Makoto
Makino, Kana
Igawa, Kazunobu
Takeda, Daiki
Doiuchi, Daiki
Tomooka, Katsuhiko
Uchida, Tatsuya
Hirai, Go
author_facet Fujii, Yui
Yoritate, Makoto
Makino, Kana
Igawa, Kazunobu
Takeda, Daiki
Doiuchi, Daiki
Tomooka, Katsuhiko
Uchida, Tatsuya
Hirai, Go
author_sort Fujii, Yui
collection PubMed
description 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.
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spelling pubmed-87469862022-01-11 Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst Fujii, Yui Yoritate, Makoto Makino, Kana Igawa, Kazunobu Takeda, Daiki Doiuchi, Daiki Tomooka, Katsuhiko Uchida, Tatsuya Hirai, Go Molecules Communication 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. MDPI 2021-12-30 /pmc/articles/PMC8746986/ /pubmed/35011456 http://dx.doi.org/10.3390/molecules27010225 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Fujii, Yui
Yoritate, Makoto
Makino, Kana
Igawa, Kazunobu
Takeda, Daiki
Doiuchi, Daiki
Tomooka, Katsuhiko
Uchida, Tatsuya
Hirai, Go
Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title_full Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title_fullStr Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title_full_unstemmed Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title_short Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
title_sort preparation of oxysterols by c–h oxidation of dibromocholestane with ru(bpga) catalyst
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8746986/
https://www.ncbi.nlm.nih.gov/pubmed/35011456
http://dx.doi.org/10.3390/molecules27010225
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