title: Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.
abstract: [reaction: see text] An asymmetric total synthesis of (-)-swainsonine and (+)-6-epicastanospermine is described from a common intermediate, which is obtained through diastereoselective [2 + 2] cycloaddition of dichloroketene to a chiral enol ether.
authors.affiliation: Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Ceccon
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Greene
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Poisson
mesh_terms: D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines
chemical_list: D007212:Indolizines; D017026:Swainsonine; C037806:castanospermine; D054836:Indolizidines