Stereoselective synthesis of fluoro-homoneplanocin A as a potential antiviral agent

Org Lett. 2012 Apr 20;14(8):2134-7. doi: 10.1021/ol300667q. Epub 2012 Apr 11.

Abstract

Fluoro-homoneplanocin A (4) was synthesized from d-ribose, via the enyne ring-closing metathesis of 9, the stereoselective opening of epoxide 23a with fluoride, and a simultaneous oxidation-elimination reaction. The key intermediate 8 is expected to serve as a versatile intermediate for the synthesis of carbanucleosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Adenosine / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Aspergillus niger / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Ribose / chemistry*
  • Stereoisomerism

Substances

  • Antiviral Agents
  • fluoro-homoneplanocin A
  • Ribose
  • neplanocin A
  • Adenosine