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Issue 16, 2000
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Pyrrolidinones derived from (S )-pyroglutamic acid. Part 1. Conformationally constrained glutamate

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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.

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Article information


Submitted
13 Mar 2000
Accepted
02 Jun 2000
First published
21 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2783-2792
Article type
Paper

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

J. H. Bailey, D. T. Cherry, J. Dyer, M. G. Moloney, M. J. Bamford, S. Keeling and R. B. Lamont, J. Chem. Soc., Perkin Trans. 1, 2000, 2783
DOI: 10.1039/B001999M

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