title: Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of beta-D-xylo, beta-D-ribo, beta-L-arabino, and beta-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols.
abstract: The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta-D-xylofuranose, 4a-carba-beta-D-ribofuranose, 4a-carba-beta-L-arabinofuranose, and 4a-carba-beta-L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta-D-xylofuranosyl)thiol, (4a-carba-beta-D-ribofuranosyl)thiol, (4a-carba-beta-L-arabinofuranosyl)thiol, and (4a-carba-beta-L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.
authors.affiliation: Istituto per l'Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, I-07100 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: V
authors.initials: V
authors.lastname: Zambrano
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