Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals

Org Biomol Chem. 2009 Apr 7;7(7):1284-7. doi: 10.1039/b823099b. Epub 2009 Feb 11.

Abstract

The flexible installations of a sulfamate ester on a glycal scaffold at C3, C4, or C6 approaching alpha- or beta-aminoglycosides is communicated. A variety of glycal acceptors (O, S, and N) were applied, enhancing the utility of this method as an operationally simple protocol for the stereoselective synthesis of polyfunctionalized alpha- or beta- aminosaccharides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / chemistry
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Catalysis
  • Glycosides / chemistry*
  • Glycosylation
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Aminoglycosides
  • Aziridines
  • Glycosides
  • Rhodium