5-exo Radical cyclization onto 3-alkoxyketimino-1, 6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin

J Org Chem. 2000 Sep 22;65(19):5960-8. doi: 10.1021/jo000325y.


Ketoxime ethers at C3 of 1,6-anhydro-beta-D-mannopyranose derivatives were found to be useful 5-exo radical traps of alkyl and vinyl radicals generated at a chain tethered to the C2 hydroxyl group, allowing advanced synthetic intermediates for (-)-tetrodotoxin to be prepared from D-mannose in good overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Cyclization
  • Mannose / analogs & derivatives*
  • Mannose / chemical synthesis*
  • Molecular Conformation
  • Morpholines / chemical synthesis
  • Morpholines / chemistry
  • Stereoisomerism
  • Tetrodotoxin / chemistry*
  • Vinyl Compounds / chemistry


  • Morpholines
  • Vinyl Compounds
  • Tetrodotoxin
  • Mannose