Carbapenem and Penem Antibiotics. VI. Synthesis and Antibacterial Activity of 2-Heteroaromatic-thiomethyl and 2-Carbamoyloxymethyl 1-Methylcarbapenems

Mitsuru IMUTA; Hikaru ITANI; Hisao ONA; Yoshinori HAMADA; Shoichiro UYEO; Tadashi YOSHIDA

doi:10.1248/cpb.39.663

Mitsuru IMUTA, Hikaru ITANI, Hisao ONA, Yoshinori HAMADA, Shoichiro UYEO, Tadashi YOSHIDA

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Keywords: β-lactam antibiotic, carbapenem antibiotic, 1α-methyl carbapenem antibiotic, 1β-methyl carbapenem antibiotic, 1, 1-dimethyl carbapenem antibiotic, 2-functionalized-methyl carbapenem antibiotic, Zn-promoted allylation, antibacterial activity, methicillin-resistant S. aureus (MRSA)

JOURNAL FREE ACCESS

1991 Volume 39 Issue 3 Pages 663-671

DOI https://doi.org/10.1248/cpb.39.663

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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.

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