title: Total synthesis of (-)-caprazamycin A.
abstract: Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features a) the scalable preparation of the syn-β-hydroxy amino acid with a thiourea-catalyzed diastereoselective aldol reaction, b) construction of a diazepanone with an unstable fatty-acid side chain, and c) global deprotection with hydrogenation. This report provides a route for the synthesis of related liponucleoside antibiotics with fatty-acid side chains.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
authors.forename: Hugh
authors.initials: H
authors.lastname: Nakamura
authors.forename: Chihiro
authors.initials: C
authors.lastname: Tsukano
authors.forename: Motohiro
authors.initials: M
authors.lastname: Yasui
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Yokouchi
authors.forename: Masayuki
authors.initials: M
authors.lastname: Igarashi
authors.forename: Yoshiji
authors.initials: Y
authors.lastname: Takemoto
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000995:Antitubercular Agents; D001381:Azepines; C512217:caprazamycin A; D014529:Uridine
keywords: aldol reaction; antibiotics; natural products; organocatalysis; total synthesis