New synthetic approach to enantiopure bicyclic sulfonium salts: swainsonine analogues.
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.
Cerè
Vanda
V
Department of Organic Chemistry, A. Mangini University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy. cere@ms.fci.unibo.it
Pollicino
Salvatore
S
Ricci
Alfredo
A
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
D005944:Glucosamine; D007202:Indicators and Reagents; D007212:Indolizines; D013452:Sulfonium Compounds; D017026:Swainsonine; C478924:1-deoxy-nojirimycin; C037806:castanospermine; D054836:Indolizidines