title: Total Synthesis of (±)-Integrifolin.
abstract: The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan.
authors.forename: Katsuya
authors.initials: K
authors.lastname: Shimomaki
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, 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, 152-8851, Japan. niwasawa@chem.titech.ac.jp.
authors.forename: Nobuharu
authors.initials: N
authors.lastname: Iwasawa
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D004987:Ethers
keywords: alkenes; cyclization; sesquiterpenoids; total synthesis; tungsten