title: Synthesis of enantiopure 2-C-glycosyl-3-nitrochromenes.
abstract: A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of the sugar-derived (Z)-1-bromo-1-nitroalkenes with o-hydroxybenzaldehydes afforded enantiopure (2S,3S,4S)-3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans, which, upon SmI2-promoted β-elimination, yielded chiral enantiopure 2-C-glycosyl-3-nitrochromenes.
authors.affiliation: Department of Chemistry & QOPNA, University of Aveiro , 3810-193 Aveiro, Portugal.
authors.forename: Raquel G
authors.initials: RG
authors.lastname: Soengas
authors.forename: Humberto
authors.initials: H
authors.lastname: Rodríguez-Solla
authors.forename: Artur M S
authors.initials: AM
authors.lastname: Silva
authors.forename: Ricardo
authors.initials: R
authors.lastname: Llavona
authors.forename: Filipe A Almeida
authors.initials: FA
authors.lastname: Paz
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002839:Chromans / Q000737:chemistry*; D004980:Ethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D002839:Chromans; D009574:Nitro Compounds; C533588:bromonitromethane; D004980:Ethane