Stereoselective synthesis of the viridiofungin analogue NA808 from a chiral tetrahydrofuran-carboxylic acid

Org Biomol Chem. 2017 Aug 9;15(31):6632-6639. doi: 10.1039/c7ob01608e.

Abstract

The viridiofungin analogue NA808 was synthesized by the stereoselective Ireland-Claisen rearrangement of dienylmethyl ester, regioselective bromolactonization of β-divinylpropanoic acid and retro-bromolactonization.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry*
  • Citrates / chemical synthesis*
  • Citrates / chemistry*
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Halogenation
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Stereoisomerism
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis
  • Tyrosine / chemistry

Substances

  • Antiviral Agents
  • Carboxylic Acids
  • Citrates
  • Furans
  • Lactones
  • NA808
  • viridiofungin A
  • tetrahydrofuran
  • Tyrosine