Diastereoselective synthesis of (2R,4R)-2-aryl-4-hydroxypyrrolidine: preparation of the side chain of novel carbapenem.
Improved synthesis of the trans-3,5-disubstituted pyrrolidin-3-ylthio side-chain of the novel carbapenem 1 was achieved via stereoselective reduction of the 1-aryl-1-butanone derivative 5 and successive intramolecular cyclization of the resulting chiral alcohol 6. The 1-aryl-1-butanone derivative 5 was obtained by a coupling reaction of protected 4-hydroxy-2-pyrrolidone with aryl-Grignard reagent.
Hashihayata
T
T
Banyu Tsukuba Research Institute, Ibaraki, Japan. hshytatk@banyu.co.jp
Sakoh
H
H
Goto
Y
Y
Hirose
M
M
Sakuraba
S
S
Imamura
H
H
Sugimoto
Y
Y
Yamada
K
K
Morishima
H
H
D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D015780:Carbapenems