Issue 15, 2005

Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid

Abstract

Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala–Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of the stereochemistry of the synthetic intermediates.

Graphical abstract: Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid

Article information

Article type
Paper
Submitted
18 Mar 2005
Accepted
01 Jun 2005
First published
01 Jul 2005

Org. Biomol. Chem., 2005,3, 2872-2882

Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid

E. L. Bentz, R. Goswami, M. G. Moloney and S. M. Westaway, Org. Biomol. Chem., 2005, 3, 2872 DOI: 10.1039/B503994K

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