title: Asymmetric total synthesis of pseurotin A.
abstract: The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD). [reaction: see text]
authors.affiliation: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shoji
authors.forename: Shinpei
authors.initials: S
authors.lastname: Yamaguchi
authors.forename: Takasuke
authors.initials: T
authors.lastname: Mukaiyama
authors.forename: Junichiro
authors.initials: J
authors.lastname: Yamaguchi
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kakeya
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Osada
mesh_terms: D001597:Benzylidene Compounds / Q000737:chemistry; D003500:Cyclization; D007769:Lactams / Q000737:chemistry; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001597:Benzylidene Compounds; D007769:Lactams; D011760:Pyrrolidinones; C012013:pseurotin