Expeditious synthesis of a common intermediate of L-1-deoxyallonojirimycin and L-1-deoxymannojirimycin

J Org Chem. 2009 Mar 6;74(5):2238-41. doi: 10.1021/jo802757f.

Abstract

The expeditious synthesis of a common intermediate of L-1-deoxyallonojirimycin (L-allo-DNJ) and L-1-deoxymannojirimycin (L-manno-DNJ) is reported. This intermediate is obtained in highly diastereo- and enantioselectivity with 38.4% overall yield in six steps involving the unprecedented ring-closing metathesis of a tert-butylsulfinyl allylamine as the key step.

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives*
  • 1-Deoxynojirimycin / chemical synthesis
  • 1-Deoxynojirimycin / chemistry
  • Allylamine / analogs & derivatives*
  • Allylamine / chemistry*
  • Cyclization
  • Molecular Conformation
  • Stereoisomerism

Substances

  • L-1-deoxyallonojirimycin
  • L-1-deoxymannojirimycin
  • 1-Deoxynojirimycin
  • Allylamine