title: Exploitation of in situ generated sugar-based olefin keto-nitrones: synthesis of carbocycles, heterocycles, and nucleoside derivatives.
abstract: Application of intramolecular 1,3-dipolar nitrone cycloaddition reaction on carbohydrate-derived precursors containing an olefin functionality at C-1 or C-3 or C-5 and a nitrone moiety at C-2 or C-3 as appropriate has resulted in the formation of structurally new cycloaddition products containing furanose-fused oxepane, thiepane, azepane, cyclopentane, cycloheptane, tetrahydrofuran, and pyranose-fused tetrahydrofuran rings. The structure and stereochemistry of these products have been characterized by spectral as well as single-crystal X-ray analyses. Two of the compounds have been transformed to the bicyclic nucleoside derivatives applying Vorbrüggen reaction conditions.
authors.forename: Soumendra Nath
authors.initials: SN
authors.lastname: Das
authors.forename: Arpan
authors.initials: A
authors.lastname: Chowdhury
authors.forename: Neha
authors.initials: N
authors.lastname: Tripathi
authors.forename: Prithwish K
authors.initials: PK
authors.lastname: Jana
authors.forename: Sukhendu B
authors.initials: SB
authors.lastname: Mandal
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D005663:Furans / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates; D005663:Furans; D009589:Nitrogen Oxides; D009705:Nucleosides; C015388:nitrones; C018674:tetrahydrofuran