A. Dinsmore, P. M. Doyle, D. W. Young
Jan 7, 2002
Citations
0
Influential Citations
1
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
(2S)-2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propionic acid 8, an isomer of the natural product willardiine 7, was synthesised by treatment of the pyroglutamate urea 19 with mild base followed by deprotection in a two-step modification of our ‘ring-switching’ approach to the synthesis of glutamate antagonists. Use of this two-step strategy has allowed us to synthesise L-alanine derivatives, which are β-substituted by a reduced pyrimidinedione which contains a second chiral centre. In one case, the antagonist activity at metabotropic glutamate receptors of two diastereoisomers showed little difference.