Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes: incorporation of polyhydroxylated carbocyclic beta-amino acids into peptides

Org Lett. 2003 May 1;5(9):1423-5. doi: 10.1021/ol034127f.

Abstract

A promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids, Carbocyclic / chemistry
  • Amines / chemical synthesis*
  • Amino Acids / chemistry*
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Heptanes / chemistry*
  • Hexoses / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Stereoisomerism

Substances

  • Acids, Carbocyclic
  • Amines
  • Amino Acids
  • Cyclopentanes
  • Heptanes
  • Hexoses
  • Peptides