Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene

Biosci Biotechnol Biochem. 2002 Apr;66(4):887-91. doi: 10.1271/bbb.66.887.

Abstract

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.

MeSH terms

  • Cycloleucine / analogs & derivatives*
  • Cycloleucine / chemical synthesis*
  • Cycloleucine / chemistry
  • Cycloleucine / pharmacology
  • Dicarboxylic Acids / chemical synthesis*
  • Dicarboxylic Acids / chemistry
  • Dicarboxylic Acids / pharmacology
  • Indicators and Reagents
  • Ketones / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Receptors, Metabotropic Glutamate / antagonists & inhibitors*
  • Stereoisomerism

Substances

  • Dicarboxylic Acids
  • Indicators and Reagents
  • Ketones
  • Receptors, Metabotropic Glutamate
  • Cycloleucine
  • 1-amino-1,3-dicarboxycyclopentane