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

Abstract:
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.
Publication status:
Published

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Publisher copy:
10.1039/b001999m

Authors


Bailey, JH More by this author
Cherry, DT More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Bamford, MJ More by this author
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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
16
Pages:
2783-2792
Publication date:
2000
DOI:
EISSN:
1364-5463
ISSN:
1470-4358
URN:
uuid:7d5d6141-5e60-442b-89fd-da191bbdf8d7
Source identifiers:
37528
Local pid:
pubs:37528
Language:
English

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