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

T Hashihayata, H Sakoh, Y Goto, K Yamada…

文献索引：Hashihayata, Takashi; Sakoh, Hiroki; Goto, Yasuhiro; Yamada, Koji; Morishima, Hajime Chemical and pharmaceutical bulletin, 2002 , vol. 50, # 3 p. 423 - 425

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被引用次数: 7

摘要

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 ultra-broad-spectrum carbapenem 1, via (2R, 4R)-2-aryl-4-hydroxypyrrolidine 7.