Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties

•Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.•Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.•The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate.Figure optionsDownload full-size imageDownload as PowerPoint slide

Graphical abstractThe tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate.Figure optionsDownload full-size imageDownload as PowerPoint slide