title: Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.
abstract: L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ (UK) http://www.tomsheppard.eu.
authors.forename: Robert W
authors.initials: RW
authors.lastname: Foster
authors.affiliation: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, SG1 2NY (UK).
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Tame
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ (UK) http://www.tomsheppard.eu.
authors.forename: Dejan-Krešimir
authors.initials: DK
authors.lastname: Bučar
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ (UK) http://www.tomsheppard.eu. h.c.hailes@ucl.ac.uk.
authors.forename: Helen C
authors.initials: HC
authors.lastname: Hailes
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ (UK) http://www.tomsheppard.eu. tom.sheppard@chem.ucl.ac.uk.
authors.forename: Tom D
authors.initials: TD
authors.lastname: Sheppard
mesh_terms: D001089:Arabinose / Q000737:chemistry*; D003500:Cyclization; D003681:Dehydration; D005663:Furans / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D009116:Muscarine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010429:Pentoses / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000608091:3-hydroxymuscarine; D005663:Furans; D006835:Hydrazones; D010429:Pentoses; D009116:Muscarine; D001089:Arabinose
keywords: arabinose; biomass; cyclization; hydrazines; tetrahydrofurans