The biosynthesis of the maleimide ring of showdomycin (1) from L-glutamic acid proceeds with retention of the 3-pro-S-hydrogen at the vinylic position of showdomycin, whilst the 3-pro-R-hydrogen is lost.
J. G. Buchanan, A. Kumar, R. H. Wightman, S. J. Field and D. W. Young, J. Chem. Soc., Chem. Commun., 1984, 1517 DOI: 10.1039/C39840001517
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