Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent

J Org Chem. 2008 Sep 5;73(17):6657-65. doi: 10.1021/jo800769m. Epub 2008 Jul 29.

Abstract

A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology*
  • DNA Viruses / drug effects*
  • DNA Viruses / growth & development
  • Esterification
  • Humans
  • Lactams / chemistry*
  • Magnetic Resonance Spectroscopy
  • Pyrrolidines / chemistry
  • RNA Viruses / drug effects*
  • RNA Viruses / growth & development
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Antiviral Agents
  • Lactams
  • Pyrrolidines
  • pantolactone
  • 4-Butyrolactone