Synthesis and photochemistry of 5-hydroxy-5β-cholest-3-en-6-one
✍ Scribed by Shirley Stiver; Peter Yates
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 184 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Reaction of 36-benzyloxy-5-hydroxy-5a-cholestan-6-one (1) with potassium t-butoxide in t-butyl alcohol gives 5-hydroxy-56-cholest-3-en-6-one (2), which on direct irradiation (300 nm) ?-n hexanes gives the B-seco steroid 9 and the indenacetaldehyde derivative 10.
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Oxidized LDL exhibits cytotoxic activity towards endothelial cells, which is thought to be mediated by the products derived also from cholesterol oxidation, mainly involving the B-ring. By LC-PB-EI-MS and El-MS/MS analysis, we have identified 3fl-hydroxy-5~-cholest-6-ene-5-hydroperoxide among the ch
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Although most cholestenes of the 56 series have been throughly investigatea' only few informations can be found in the literature about the analogous 5P-derivatives. It has been reported, for instance, that 5)3-cholestan-3/j-01 tosylate is transformed by alumina into 5P-cholest-2-ene,' and that the