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

Julien Ceccon; Andrew E Greene; Jean-François Poisson

doi:10.1021/ol0617751

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

Org Lett. 2006 Oct 12;8(21):4739-42. doi: 10.1021/ol0617751.

Authors

Julien Ceccon¹, Andrew E Greene, Jean-François Poisson

Affiliation

¹ Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France.

PMID: 17020291
DOI: 10.1021/ol0617751

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Indolizines / chemical synthesis*
Indolizines / chemistry
Molecular Structure
Stereoisomerism
Swainsonine / chemical synthesis*
Swainsonine / chemistry

Substances

Indolizines
castanospermine
Swainsonine