title: Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems.
abstract: The synthesis and antibacterial activity of the 1-methylcarbapenems, 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl derivatives having a 6-[(R)-1-hydroxyethyl] side chain, are described. The introduction of a methyl substituent at the C-1 position was accomplished by a newly developed procedure using crotyl halides and zinc dust. The 2-hydroxymethyl carbapenems as key intermediates allowed an easy entry into the preparation of title carbapenems.
authors.affiliation: Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Imuta
authors.forename: H
authors.initials: H
authors.lastname: Itani
authors.forename: H
authors.initials: H
authors.lastname: Ona
authors.forename: Y
authors.initials: Y
authors.lastname: Hamada
authors.forename: S
authors.initials: S
authors.lastname: Uyeo
authors.forename: T
authors.initials: T
authors.lastname: Yoshida
mesh_terms: D000818:Animals; D015780:Carbapenems / Q000138:chemical synthesis* / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice
chemical_list: D015780:Carbapenems; D006571:Heterocyclic Compounds