title: 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.
authors.affiliation: Queen's University Belfast, School of Pharmacy, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK.
authors.forename: Philip
authors.initials: P
authors.lastname: Redpath
authors.affiliation: Queen's University Belfast, School of Pharmacy, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK; Queen's University Belfast, Centre for Cancer Research and Cell Biology, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK.
authors.forename: Kerry A
authors.initials: KA
authors.lastname: Ness
authors.affiliation: Queen's University Belfast, School of Pharmacy, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK.
authors.forename: Joanne
authors.initials: J
authors.lastname: Rousseau
authors.affiliation: GlaxoSmithKline, Stevenage SG1 2NY, UK.
authors.forename: Simon J F
authors.initials: SJ
authors.lastname: Macdonald
authors.affiliation: Queen's University Belfast, School of Pharmacy, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK; Queen's University Belfast, Centre for Cancer Research and Cell Biology, Lisburn Road, Belfast BT9 7BL, Northern Ireland, UK. Electronic address: m.migaud@qub.ac.uk.
authors.forename: Marie E
authors.initials: ME
authors.lastname: Migaud
mesh_terms: D019817:Benzoic Acid / Q000737:chemistry; D019298:Glucose-6-Phosphate / Q000031:analogs & derivatives / Q000737:chemistry; D006027:Glycosides; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C438934:C-glycoside; D006027:Glycosides; D009005:Monosaccharides; C015785:2-deoxyglucose-6-phosphate; D019298:Glucose-6-Phosphate; D019817:Benzoic Acid
keywords: C-Glycoside; C-Nucleoside; Glucose-6-phosphate bioisostere; Tandem ene/intramolecular Sakurai cyclisation; Transmetallation