| Literature DB >> 18996406 |
Shoujiro Ogawa1, Genta Kakiyama, Akina Muto, Atsuko Hosoda, Kuniko Mitamura, Shigeo Ikegawa, Alan F Hofmann, Takashi Iida.
Abstract
Experiments were performed to compare the regioselective hydroxylation of the isopropyl C-H bond at C-25 in 5alpha-cholestan-3beta-yl acetate by in situ generated dimethyldioxirane, methyl(trifluoromethyl)dioxirane, hexafluoro(dimethyl)dioxirane or ethyl(trifluoromethyl)dioxirane (ETDO). The dioxiranes were generated from the corresponding ketones and potassium peroxymonosulfate in aq. NaHCO(3), pH 7.5-8.0. Of the four dioxiranes examined, partially fluorinated, sterically bulky ETDO displayed the highest reactivity and regioselectivity. Using in situ generated ETDO, a facile, synthesis was developed for two naturally occurring oxysterols, i.e., 25-hydroxycholesterol, as well as its 3-sulfate (overall yield of the sulfate, 24%) and 24-oxocholesterol (16%), starting from cholesterol.Entities:
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Year: 2008 PMID： 18996406 DOI： 10.1016/j.steroids.2008.09.015
Source DB: PubMed Journal: Steroids ISSN： 0039-128X Impact factor: 2.668