Abstract
A novel synthetic route to 2,3,4-trideoxy-4,4-difluoro-β-d -ribo -hexopyranose
adenosine and 2,3,4-trideoxy-2,3-didehydro-4,4-difluoro-β-d -ribo -hexopyranose
adenosine has been developed. The approach highlights the highly
regio- and stereoselective palladium-catalyzed glycosylation of
Boc-protected pyranose, which was prepared from the oxidation-cyclization
of a difluorinated diol. The diol was provided through ozonization
and Lindlar reduction of optically pure enynic alcohol.
Key words
nucleosides - fluorinated compounds - palladium-catalyzed
glycosylation
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