Catalytic Asymmetric Synthesis of a 1-Deoxy-1,1-difluoro-d-xylulose

A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted al...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 3; pp. 337 - 339
Main Authors Cox, Liam R, DeBoos, Gareth A, Fullbrook, Jeremy J, Percy, Jonathan M, Spencer, Neil S, Tolley, Malcolm
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.02.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Magnetic Resonance Spectroscopy
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Xylulose - analogs & derivatives
Xylulose - chemical synthesis
Xylulose - chemistry
DIHYDROXYLATION
1-DEOXY-D-XYLULOSE
REARRANGEMENTS
DERIVATIVES
2-ULOSES
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Summary:A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0273553