Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction.
Compounds 2 and 3 were designed in order to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection.
Giacobbe
S A
SA
GlaxoWellcome S.p.A., Medicines Research Center, Verona, Italy.
Baraldi
D
D
Di Fabio
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R
D002851:Chromatography, High Pressure Liquid; D018691:Excitatory Amino Acid Antagonists / Q000138:chemical synthesis*; D005998:Glycine / Q000037:antagonists & inhibitors*; D007783:Lactones / Q000737:chemistry; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors / Q000737:chemistry*
D018691:Excitatory Amino Acid Antagonists; D007783:Lactones; D016194:Receptors, N-Methyl-D-Aspartate; D005998:Glycine