Acessibilidade / Reportar erro
Communication • J. Braz. Chem. Soc. 21 (5) • 2010 • https://doi.org/10.1590/S0103-50532010000500002   copy

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

Authorship SCIMAGO INSTITUTIONS RANKINGS

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).

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

Sociedade Brasileira de Química Instituto de Química - UNICAMP, Caixa Postal 6154, 13083-970 Campinas SP - Brazil, Tel./FAX.: +55 19 3521-3151 - São Paulo - SP - Brazil
E-mail: office@jbcs.sbq.org.br
Acompanhe os números deste periódico no seu leitor de RSS