A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid

Journal of the Brazilian Chemical Society

Evanoel Crizanto De Lima²  Paulo G. De Lima¹  Carolina C. De Souza²  Marta C. L. S. Maior²  Ayres G. Dias¹  Paulo R. R. Costa² 

[1] ,Universidade Federal do Rio de Janeiro Centro de Ciências da Saúde Núcleo de Pesquisas de Produtos NaturaisRio de Janeiro RJ ,Brazil

关键词: stereoselective synthesis;    chemoselective acyl substitution;    aspartic acid diester;    neuroactive amino acid;    NMDA;    L-tryptophan metabolism;   

DOI  :  10.1590/S0103-50532010000500002

来源: SciELO

【 摘 要 】

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).

【 授权许可】

CC BY   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License