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

Autor:	Steve Keeling, David T. Cherry, Mark G. Moloney, Jonathan H. Bailey, R. Brian Lamont, Mark J. Bamford, James Dyer
Rok vydání:	2000
Předmět:	Agonist chemistry.chemical_compound chemistry Bicyclic molecule medicine.drug_class Stereochemistry medicine Lactam NMDA receptor Total synthesis Pyroglutamic acid Pyrrolidinones Ring (chemistry)
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :2783-2792
ISSN:	1364-5463 1470-4358
DOI:	10.1039/b001999m
Popis:	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 are particularly effective in this regard. The bicyclic ring system both controls and permits the determination of ring stereochemistry. The utility of this methodology is demonstrated by a formal total synthesis of the NMDA receptor agonist, CPAA 11. © The Royal Society of Chemistry 2000.
Databáze:	OpenAIRE
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