An Efficient C−H Oxidation Protocol for α-Hydroxylation of Cyclic Steroidal Ethers

Various C-16 hydroxy steroids have been prepared with the aid of CrO3/Bu4NIO4. Out of the two possible reaction courses, transition state B is favored because of less steric interference between substrate and CrO4. Thus, C−H bonds at C-16 are oxidized selectively.

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 9; pp. 1437 - 1440
Main Authors Lee, Seongmin, Fuchs, Philip L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.04.2004
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Electrons
Ethers, Cyclic - chemical synthesis
Hydroxylation
Molecular Conformation
Oxidation-Reduction
Physical Sciences
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Steroids - chemical synthesis
Steroids - chemistry
MILD
METHYL(TRIFLUOROMETHYL)DIOXIRANE
PERIODIC ACID
CATALYZED OXIDATION
BONDS
PEROXO COMPLEXES
OXYFUNCTIONALIZATION
DIMETHYLDIOXIRANE
CHROMIUM
EPOXIDATION
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Summary:Various C-16 hydroxy steroids have been prepared with the aid of CrO3/Bu4NIO4. Out of the two possible reaction courses, transition state B is favored because of less steric interference between substrate and CrO4. Thus, C−H bonds at C-16 are oxidized selectively.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049712a