Synthesis of the antimalarial drug FR900098 utilizing the nitroso-ene reaction

Org Lett. 2007 Oct 11;9(21):4379-82. doi: 10.1021/ol702082k. Epub 2007 Sep 22.

Abstract

The antimalarial drug FR900098 was prepared from diethyl allylphosphonate involving the nitroso-ene reaction with nitrosocarbonyl methane as the key step followed by hydrogenation and dealkylation. The utilization of dibenzyl allylphosphonate as the starting compound allows one-step hydrogenation with dealkylation, which simplifies the preparative scheme further.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Fosfomycin / analogs & derivatives*
  • Fosfomycin / chemical synthesis
  • Fosfomycin / chemistry
  • Fosfomycin / pharmacology
  • Hydrogenation
  • Molecular Structure
  • Nitroso Compounds / chemistry*
  • Organophosphonates / chemistry*
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Nitroso Compounds
  • Organophosphonates
  • Fosfomycin
  • 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid