A versatile and stereocontrolled route to pyranose and furanose C-glycosides
Joanne E Harvey1, Steven A Raw, Richard J K Taylor
1Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. joanne.harvey@vuw.ac.nz
Abstract:
[reaction: see text] The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.
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