Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Org Biomol Chem. 2016 May 11;14(19):4488-98. doi: 10.1039/c6ob00531d.

Abstract

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

MeSH terms

  • Carbohydrate Conformation
  • Chemistry Techniques, Synthetic
  • Models, Molecular
  • Pyrrolidines / chemistry*
  • Stereoisomerism
  • Sugars / chemical synthesis*
  • Sugars / chemistry*
  • Swainsonine / chemical synthesis*
  • Swainsonine / chemistry*

Substances

  • Pyrrolidines
  • Sugars
  • pyrrolidine
  • Swainsonine