A versatile and stereocontrolled route to pyranose and furanose C-glycosides.Org Lett. 2004 Jul 22; 6(15):2611-4.OL
[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.