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

Abstract

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.

Keywords: C-Glycoside; C-Nucleoside; Glucose-6-phosphate bioisostere; Tandem ene/intramolecular Sakurai cyclisation; Transmetallation.