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Note | Regular issue | Vol 51, No. 2, 1999, pp.365-372
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8403
Ex-Chiral Pool Synthesis of Aminooxazepinones as Conformationally Restricted β-Amino Acid Analogs

Dorothee Michel, Reiner Waibel, and Peter Gmeiner*

*Institut für Pharmazie und Lebensmittelchemie, Universität Erlangen-Nürnberg, Schuhstrasse 19, D-91052 Erlangen, Germany

Abstract

Starting from natural asparagine, an efficient synthesis of the dibenzyl protected 6-amino-1,3-oxazepin-4-one (7) is reported. According to NMR based conformational studies, the lactam-bridged β-amino acid analog (7) adopts preferentially a twisted boat structure. The incorporation of the described molecular scaffold to give a constrained β-analog of the dopamine receptor modulating peptide Pro-Leu-Gly-NH2 is described as an application in the field of medicinal chemistry.