Abstract
A formal synthesis of Thienamycin from ethyl (E)–crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N–O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton. Subsequent transformations of the five-membered ring substituents provide the title compound.
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Acknowledgements
Financial support by the European Union within European Regional Development Fund, Project POIG.01.01.02.-14-102/09 is gratefully acknowledged. MP thanks the National Science Centre for PRELUDIUM grant (2014/13/N/ST5/01758).
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Pieczykolan, M., Furman, B. & Chmielewski, M. Formal synthesis of Thienamycin. J Antibiot 70, 781–787 (2017). https://doi.org/10.1038/ja.2017.44
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DOI: https://doi.org/10.1038/ja.2017.44
