Synthetic Carbapenem Antibiotics. I. 1-b-Methylcarbapenem

Shih, David H.; Baker, Florence; Cama, L. D.; Chrisrtensen, Burton G.

doi:10.3987/s-1984-01-0029

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1992

2022

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Cited by 197 publications

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“…S1 in the supplemental material), which vary structurally at the C2 position. In addition, a C1β-methyl group was introduced, which improves stability against human renal dehydropeptidase (DHP-1) compared to the first clinical carbapenem, imipenem ( 17 ). The scaffold has not been significantly altered in the past 2 decades, apart from modifications at the C2 position.…”

Section: Introductionmentioning

confidence: 99%

C6 Hydroxymethyl-Substituted Carbapenem MA-1-206 Inhibits the Major Acinetobacter baumannii Carbapenemase OXA-23 by Impeding Deacylation

Stewart

Tóth

Alqurafi

et al. 2022

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Section: Introductionmentioning

confidence: 99%

C6 Hydroxymethyl-Substituted Carbapenem MA-1-206 Inhibits the Major Acinetobacter baumannii Carbapenemase OXA-23 by Impeding Deacylation

Stewart

Tóth

Alqurafi

et al. 2022

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Synthesis of 1β-Methylcarbapenem Antibiotic Precursors by Cyclization Using π-Allylpalladium Complexes

et al. 1999

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An efficient diastereoselective multi‐step synthesis of bicyclic 1β‐methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4‐acetoxyazetidin‐2‐one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β‐stereochemistry at the 1‐position, and a π‐allylpalladium ring‐closure strategy is used to form the functionalized carbapenem skeleton.

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