Synthesis of the side chain of a novel carbapenem via iodine-mediated oxidative cyclization of (1R)-N-(1-aryl-3-butenyl)acetamide.
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.
Hashihayata
Takashi
T
Banyu Tsukuba Research Institute, Ibaraki, Japan. hshytatk@banyu.co.jp
Sakoh
Hiroki
H
Goto
Yasuhiro
Y
Yamada
Koji
K
Morishima
Hajime
H
D000081:Acetamides / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction; D013057:Spectrum Analysis
D000081:Acetamides; D015780:Carbapenems; D007455:Iodine