title: A palladium-catalyzed carbo-oxygenation: the bielschowskysin case.
abstract: An asymmetric synthesis of an advanced tetracyclic intermediate toward the synthesis of bielschowskysin (1) is described. A biomimetic [2 + 2]-photocyclization was used to establish the cyclobutane core of bielschowskysin. Macrocyclization under Heck conditions led to an unprecedented carbo-oxygenation of a 1,1-disubstituted double bond.
authors.affiliation: University of Vienna , Department of Organic Chemistry, Währinger Str. 38, 1090 Vienna, Austria.
authors.forename: Martin
authors.initials: M
authors.lastname: Himmelbauer
authors.forename: Jean-Baptiste
authors.initials: JB
authors.lastname: Farcet
authors.forename: Julien
authors.initials: J
authors.lastname: Gagnepain
authors.forename: Johann
authors.initials: J
authors.lastname: Mulzer
mesh_terms: D002384:Catalysis; D003503:Cyclobutanes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003503:Cyclobutanes; D004224:Diterpenes; D011083:Polycyclic Compounds; C494537:bielschowskysin; D010165:Palladium