
%0 Journal Article
%A Cox, Matthew 
%A Jahangiri, Saba 
%A Perkins, Michael V. 
%A Prager, Rolf H. 
%T Some Synthetic Approaches to Glutamate AMPA Receptor Agonists Based on Isoxazolones
%J Australian Journal of Chemistry
%D 2004/07/07
%V 57
%N 7
%P 685-688
%K 
%R https://doi.org/10.1071/CH04041
%U https://www.publish.csiro.au/paper/CH04041 
%X Several approaches to the synthesis of derivatives of the antifungal antibiotic TAN-950A, which is also an agonist of glutamate at hippocampal neurons, are reported. Additions of isoxazolon-4-yl anions to methyleneoxazolidinones were not useful because addition occurred predominantly through N-2. Similarly addition of the isoxazolon-4-yl radicals to model Michael acceptors occurred predominantly through N-2. Racemic analogues of TAN-950A were prepared by reaction of isoxazolone Mannich bases with acetylaminomalonate or addition of &#946;-ketoester anions to dehydroalanines. The best approach to enantiomerically pure analogues was by acylation of pyroglutamates, followed by reaction with hydroxylamine. 
