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  • Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.

Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.

Organic letters (2006-10-06)
Julien Ceccon, Andrew E Greene, Jean-François Poisson
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%