326891-09-2Relevant articles and documents
Use of a modified ring-switching strategy to synthesise the glutamate antagonist (2s)-2-amino-3-(2,4- oxo-1,2,3,4-tetra-hydropyrimidin-5-yl)propionate and related compounds with two chiral centres
Dinsmore, Andrew,Doyle, Paul M.,Young, Douglas W.
, p. 155 - 164 (2007/10/03)
(2S)-2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propionic acid8, an isomer of the natural product willardiine7, 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.
