
TY  - JOUR
A1  - Cox, Matthew 
A1  - Jahangiri, Saba 
A1  - Perkins, Michael V. 
A1  - Prager, Rolf H. 
T1  - Some Synthetic Approaches to Glutamate AMPA Receptor Agonists Based on Isoxazolones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 7
SP  - 685
EP  - 688
KW  - 
UR  - https://doi.org/10.1071/CH04041 
N2  - 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. 
ER  -

