title: Stereodivergent synthesis of diastereoisomeric carba analogs of glycal-derived vinyl epoxides: a new access to carbasugars.
abstract: A convenient method for the stereoselective synthesis of diasteroisomeric vinyl epoxides (-)-2α and (-)-2β, the carba analogs of D-galactal and D-allal-derived vinyl epoxides 1α and 1β, has been elaborated starting from tri-O-acetyl-D-glucal. The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)-3b, which allows to switch the glycal structure into the corresponding carba analog scaffold. Epoxides (-)-2α and (-)-2β derive from the same synthetic intermediate, the trans diol (+)-5.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Pisa, Pisa, Italy.
authors.forename: Ileana
authors.initials: I
authors.lastname: Frau
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Lucilla
authors.initials: L
authors.lastname: Favero
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D054329:Carbasugars; D004852:Epoxy Compounds; C002038:galactal; D005690:Galactose