First enantiospecific synthesis of a 3,4-dihydroxy-L-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist.

@article{Dauban2000FirstES,
  title={First enantiospecific synthesis of a 3,4-dihydroxy-L-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist.},
  author={Philippe Dauban and C de Saint-Fuscien and Francine C Acher and Laurent Pr{\'e}zeau and Isabelle Brabet and Jean-Philippe Pin and Robert H Dodd},
  journal={Bioorganic & medicinal chemistry letters},
  year={2000},
  volume={10 2},
  pages={129-33}
}
The first synthesis of one of the 4 possible stereoisomers of 3,4-dihydroxy-L-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown configuration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a D-ribose-derived 2,3-aziridino-gamma-lactone 4-benzyl carboxylate (6). Preliminary pharmacological studies… CONTINUE READING