Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of vitamin D3 Windaus-Grundmann ketone

The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dim...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 57; no. 19; pp. 5052 - 5054
Main Authors Bovicelli, Paolo, Lupattelli, Paolo, Mincione, Enrico, Prencipe, Teresa, Curci, Ruggero
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.09.1992
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHYL(TRIFLUOROMETHYL)DIOXIRANE
ACID
ACETONE
POTASSIUM CAROATE
INTERMEDIATE
1-ALPHA,25-DIHYDROXYERGOCALCIFEROL
DIMETHYLDIOXIRANE
EPOXIDATION
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Summary:The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue.
Bibliography:ark:/67375/TPS-MPJBP4M9-V
istex:8CBEA09EBA94CC9732128D716376CC34DF053852
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00045a004