title: Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.
abstract: We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohshima
authors.forename: Vijay
authors.initials: V
authors.lastname: Gnanadesikan
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Shibuguchi
authors.forename: Yuhei
authors.initials: Y
authors.lastname: Fukuta
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004852:Epoxy Compounds; C419325:aeruginosin 298-A; D007930:Leucine