Scalable synthesis of (+)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid as a potent and selective group II metabotropic glutamate receptor agonist

Chem Pharm Bull (Tokyo). 2007 Jan;55(1):37-43. doi: 10.1248/cpb.55.37.

Abstract

We successfully synthesized the potent and selective group II mGluR agonist (+)-1 (MGS0008) via a process incorporating the key step of efficient fluorination of epoxide (+/-)-5c. This method would be adaptable to large-scale synthesis to produce (+)-1 in multi-gram quantities.

MeSH terms

  • Bridged Bicyclo Compounds
  • Cyclohexanes / chemical synthesis*
  • Cyclohexanes / pharmacology*
  • Dicarboxylic Acids
  • Excitatory Amino Acid Agonists / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Receptors, Metabotropic Glutamate / agonists*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Bridged Bicyclo Compounds
  • Cyclohexanes
  • Dicarboxylic Acids
  • Excitatory Amino Acid Agonists
  • MGS 0008
  • Receptors, Metabotropic Glutamate