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.
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.
Sakagami
Kazunari
K
Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd., Saitama, Japan. kazunari.sakagami@po.rd.taisho.co.jp
Kumagai
Toshihito
T
Taguchi
Takeo
T
Nakazato
Atsuro
A
D001643:Bridged Bicyclo Compounds; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D003998:Dicarboxylic Acids; D018690:Excitatory Amino Acid Agonists / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D018094:Receptors, Metabotropic Glutamate / Q000819:agonists*; D021241:Spectrometry, Mass, Electrospray Ionization
D001643:Bridged Bicyclo Compounds; D003510:Cyclohexanes; D003998:Dicarboxylic Acids; D018690:Excitatory Amino Acid Agonists; C418123:MGS 0008; D018094:Receptors, Metabotropic Glutamate