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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.
Citation
Michał Pieczykolan, Bartłomiej Furman, Marek Chmielewski. Formal synthesis of Thienamycin. The Journal of antibiotics. 2017 Jun;70(6):781-787
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PMID: 28377636
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