title: New synthetic approach to enantiopure bicyclic sulfonium salts: swainsonine analogues.
abstract: The enantioselective synthesis of bicyclic sulfonium salts 8 or 9, thioanalogues of swainsonine derivatives, is described. The synthetic strategy is based on a stereo- and regiospecific transannular cyclization reaction of nine-membered cyclic sulfides, mediated by Me(3)SiI or carried out under acidic catalysis.
authors.affiliation: Department of Organic Chemistry, A. Mangini University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy. cere@ms.fci.unibo.it
authors.forename: Vanda
authors.initials: V
authors.lastname: Cerè
authors.forename: Salvatore
authors.initials: S
authors.lastname: Pollicino
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ricci
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines
chemical_list: D005944:Glucosamine; D007202:Indicators and Reagents; D007212:Indolizines; D013452:Sulfonium Compounds; D017026:Swainsonine; C478924:1-deoxy-nojirimycin; C037806:castanospermine; D054836:Indolizidines