Asymmetric total synthesis of (+)-swainsonine

Org Biomol Chem. 2011 Jan 21;9(2):531-7. doi: 10.1039/c0ob00388c. Epub 2010 Oct 19.

Abstract

A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glutamic Acid / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism
  • Swainsonine / chemical synthesis*

Substances

  • Glutamic Acid
  • Swainsonine