In connection with biosynthetic studies, the β-lactams (5; 4-HR=2H) and (5; 3-H = 4-HS=2H) have been synthesized. The 1H and 2H n.m.r. spectra of these compounds confirm the assignment of the stereochemistry to the two hydrogens at C-4 of monocyclic β-lactams such as nocardicin A. Samples of the amino-acid L-asparagine stereospecifically labelled at C-3 have been made in the course of this work.
D. Gani, D. W. Young, D. M. Carr, J. P. Poyser and I. H. Sadler, J. Chem. Soc., Perkin Trans. 1, 1983, 2811 DOI: 10.1039/P19830002811
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