title: Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: total synthesis of (±)-communiol E.
abstract: The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan. koba@chem.oit.ac.jp
authors.forename: Shoji
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Tatsuhiro
authors.initials: T
authors.lastname: Kinoshita
authors.forename: Takuji
authors.initials: T
authors.lastname: Kawamoto
authors.forename: Masato
authors.initials: M
authors.lastname: Wada
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kuroda
authors.forename: Araki
authors.initials: A
authors.lastname: Masuyama
authors.forename: Ilhyong
authors.initials: I
authors.lastname: Ryu
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D004987:Ethers; C520452:communiol E; D000432:Methanol