Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems.
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.
Imuta
M
M
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
Itani
H
H
Ona
H
H
Hamada
Y
Y
Uyeo
S
S
Yoshida
T
T
D000818:Animals; D015780:Carbapenems / Q000138:chemical synthesis* / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice
D015780:Carbapenems; D006571:Heterocyclic Compounds