Pyrrolidinones derived from (S)-pyroglutamic acid. Part 1. Conformationally constrained glutamate

作者: Jonathan H. Bailey , David T. Cherry , James Dyer , Mark G. Moloney , Mark J. Bamford

DOI: 10.1039/B001999M

关键词: NMDA receptorLactamAgonistPyroglutamic acidBicyclic moleculeStereochemistryPyrrolidinonesRing (chemistry)Total synthesisChemistry

摘要: Novel conformationally constrained pyroglutaminols and pyroglutamates are readily available using an α,β-unsaturated bicyclic lactam as a template for diastereocontrolled enolate additions in the key step; zinc enolates particularly effective this regard. The ring system both controls permits determination of stereochemistry. utility methodology is demonstrated by formal total synthesis NMDA receptor agonist, CPAA 11.

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