Tandem nucleophilic addition/cyclization reaction in the synthesis of ketimine-type iminosugars

J Org Chem. 2008 May 2;73(9):3612-5. doi: 10.1021/jo702616x. Epub 2008 Mar 22.

Abstract

The biological activity of unsaturated iminosugars has not yet been extensively studied because of a lack of general synthetic methods. A practical synthesis of these cyclic ketimine sugars was developed, which was based on a tandem addition-cyclization reaction of a Grignard reagent to a omega-methanesulfonylglycononitrile.

MeSH terms

  • Benzene / chemistry
  • Cyclization
  • Esters / chemistry
  • Imino Sugars / chemical synthesis*
  • Imino Sugars / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Esters
  • Imino Sugars
  • Pyrroles
  • Benzene