Synthesis of the side chain of a novel carbapenem via iodine-mediated oxidative cyclization of (1R)-N-(1-aryl-3-butenyl)acetamide

Chemical & Pharmaceutical Bulletin
Takashi HashihayataHajime Morishima

Abstract

A (2R,4S)-trans-disubstituted pyrrolidine ring system was constructed by employing iodine-mediated oxidative cyclization of (1R)-N-[1-(4-bromophenyl)-3-butenyl]acetamide 3 as a key step. The resulting diastereomeric mixture of (2R)-2-aryl-4-acetoxypyrrolidine 4 was stereoselectively converted to the side-chain of a novel ultrabroad-spectrum carbapenem 1, via (2R,4R)-2-aryl-4-hydroxypyrrolidine 7.

References

Mar 8, 2000·Chemical & Pharmaceutical Bulletin·H ImamuraH Morishima
Sep 26, 2000·Bioorganic & Medicinal Chemistry·H ImamuraH Morishima

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Citations

Aug 24, 2011·Antimicrobial Agents and Chemotherapy·Krisztina M Papp-WallaceRobert A Bonomo
May 1, 2021·Frontiers in Immunology·Samreen FatimaVed Prakash Dwivedi

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