title: Total Synthesis of (±)-Englerin A Using An Intermolecular [3+2] Cycloaddition Reaction of Platinum-Containing Carbonyl Ylide.
abstract: Total synthesis of (±)-Englerin A has been achieved starting from γ,δ-ynone 5 in 14 steps. The key feature of this synthesis is the highly efficient and stereoselective preparation of 8-oxabicyclo[3.2.1]octane derivative 6, a core skeleton of Englerin A, based on an inverse electron-demand [3+2] cycloaddition reaction of the platinum-containing carbonyl ylide, which was developed in our laboratory.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.|Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kusama
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Aoi
authors.initials: A
authors.lastname: Tazawa
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.|Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.
authors.forename: Kento
authors.initials: K
authors.lastname: Ishida
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan. niwasawa@chem.titech.ac.jp.
authors.forename: Nobuharu
authors.initials: N
authors.lastname: Iwasawa
mesh_terms: D061565:Cycloaddition Reaction; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010984:Platinum / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; D045789:Sesquiterpenes, Guaiane; C534971:englerin A; D010984:Platinum
keywords: [3+2] cycloaddition; carbonyl ylide; natural products; platinum; total synthesis