title: Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor.
abstract: The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2.OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized gamma-lactam moiety without protection of tert-alcohol and amide functionalities.
authors.affiliation: Department of Industrial Chemistry, Faculty of Engineering, Faculty of Science, 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: Junichiro
authors.initials: J
authors.lastname: Yamaguchi
authors.forename: Kenji
authors.initials: K
authors.lastname: Sato
authors.forename: Shinpei
authors.initials: S
authors.lastname: Yamaguchi
authors.forename: Takasuke
authors.initials: T
authors.lastname: Mukaiyama
authors.forename: Ken
authors.initials: K
authors.lastname: Sakai
authors.forename: Yukihiro
authors.initials: Y
authors.lastname: Asami
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kakeya
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Osada
mesh_terms: D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D001203:Ascomycota / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D020533:Angiogenesis Inhibitors; D011760:Pyrrolidinones; D013141:Spiro Compounds; C469812:azaspirene