title: Diastereoselective synthesis of (2R,4R)-2-aryl-4-hydroxypyrrolidine: preparation of the side chain of novel carbapenem.
abstract: 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.
authors.affiliation: Banyu Tsukuba Research Institute, Ibaraki, Japan. hshytatk@banyu.co.jp
authors.forename: T
authors.initials: T
authors.lastname: Hashihayata
authors.forename: H
authors.initials: H
authors.lastname: Sakoh
authors.forename: Y
authors.initials: Y
authors.lastname: Goto
authors.forename: M
authors.initials: M
authors.lastname: Hirose
authors.forename: S
authors.initials: S
authors.lastname: Sakuraba
authors.forename: H
authors.initials: H
authors.lastname: Imamura
authors.forename: Y
authors.initials: Y
authors.lastname: Sugimoto
authors.forename: K
authors.initials: K
authors.lastname: Yamada
authors.forename: H
authors.initials: H
authors.lastname: Morishima
mesh_terms: D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D015780:Carbapenems