title: Formal synthesis of Thienamycin.
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.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors.forename: Michał
authors.initials: M
authors.lastname: Pieczykolan
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Furman
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Chmielewski
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D013845:Thienamycins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D015780:Carbapenems; D013845:Thienamycins; C015537:thienamycin