Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.
[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.
Ceccon
Julien
J
Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France.
Greene
Andrew E
AE
Poisson
Jean-François
JF
D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines
D007212:Indolizines; D017026:Swainsonine; C037806:castanospermine; D054836:Indolizidines