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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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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Abstract 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.
AbstractList 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.
Author Curci, Ruggero
Bovicelli, Paolo
Prencipe, Teresa
Mincione, Enrico
Lupattelli, Paolo
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  surname: Curci
  fullname: Curci, Ruggero
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Keywords METHYL(TRIFLUOROMETHYL)DIOXIRANE
ACID
ACETONE
POTASSIUM CAROATE
INTERMEDIATE
1-ALPHA,25-DIHYDROXYERGOCALCIFEROL
DIMETHYLDIOXIRANE
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PublicationYear 1992
Publisher American Chemical Society
Amer Chemical Soc
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Snippet The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title 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
URI http://dx.doi.org/10.1021/jo00045a004
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