title: Variable strategy toward carbasugars and relatives. 1. Stereocontrolled synthesis of pseudo-beta-D-gulopyranose, pseudo-beta-D-xylofuranose, (pseudo-beta-D-gulopyranosyl)amine, and (pseudo-beta-D-xylofuranosyl)amine.
abstract: Four novel, chiral nonracemic carbasugars have been synthesized from 1,2-O-isopropylidene-D-glyceraldehyde. Furan- and pyrrole-based 2-silyloxy dienes--mimics of the alpha,gamma-dianions of gamma-hydroxy- and gamma-aminobutanoic acid, respectively--nicely served to complete the syntheses of two all-oxygen compounds, pseudo-beta-D-gulopyranose and pseudo-beta-D-xylofuranose, and two "anomeric" amino derivatives, (pseudo-beta-D-gulopyranosyl)amine (1,2,4-tri-epi-validamine) and (pseudo-beta-D-xylofuranosyl)amine. Two sequential, highly diastereoselective carbon-carbon bond-forming maneuvers, i.e., a vinylogous crossed aldol addition and an intramolecular aldolization, proved central to these constructions. The fact that readily available heterocyclic diene scaffolds can be employed in the assembly of a varied repertoire of carbasugars and analogues widens the prospects of dienoxy silane chemistry.
authors.affiliation: Istituto per l'Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, Sassari, Italy.
authors.forename: G
authors.initials: G
authors.lastname: Rassu
authors.forename: L
authors.initials: L
authors.lastname: Auzzas
authors.forename: L
authors.initials: L
authors.lastname: Pinna
authors.forename: L
authors.initials: L
authors.lastname: Battistini
authors.forename: F
authors.initials: F
authors.lastname: Zanardi
authors.forename: L
authors.initials: L
authors.lastname: Marzocchi
authors.forename: D
authors.initials: D
authors.lastname: Acquotti
authors.forename: G
authors.initials: G
authors.lastname: Casiraghi
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry; D008968:Molecular Conformation; D018716:Molecular Mimicry; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D003510:Cyclohexanes; D003517:Cyclopentanes; D005663:Furans; D011758:Pyrroles