Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
LIMA, Evanoel Crizanto de et al. A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid. J. Braz. Chem. Soc. [online]. 2010, vol.21, n.5, pp. 777-781. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532010000500002.
The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen full agonist of the NMDA receptors) from D-mannitol (12%, 10 steps) and by Lovey and Copper for the racemic synthesis (17%, 5 steps).
Keywords : stereoselective synthesis; chemoselective acyl substitution; aspartic acid diester; neuroactive amino acid; NMDA; L-tryptophan metabolism.