Formal synthesis of Thienamycin

  • J Antibiot (Tokyo). 2017 Jun;70(6):781-787. doi: 10.1038/ja.2017.44.
Michał Pieczykolan  1 ,  Bartłomiej Furman  1 ,  Marek Chmielewski  1
Affiliations
  • 1. Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
PMID: 28377636 DOI: 10.1038/ja.2017.44
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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