title: Synthesis of tri-, tetra-, and pentacarbonyl derivatives via ozonolysis of 1,4-dienes and cyclization to polyaromatic systems.
abstract: The aim of this work was the synthesis of polyaromatic systems by cyclization of β-polycarbonyls. Useful synthons for β-polycarbonyl derivatives are branched 1,4-dienes generated by cobalt-catalyzed hydrovinylation of terminal alkenes and 2,3-dimethyl-1,3-butadiene. Thus, a series of tri-, tetra-, and pentacarbonyl synthons was successfully synthesized. Subsequently, these synthons were examined in an ozonolysis/cyclization reaction sequence. Polyaromatic derivatives were obtained in good yields and the method was applied in the synthesis of the natural product Kwanzoquinone A.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Strasse, 435043 Marburg, Germany.
authors.forename: Laura
authors.initials: L
authors.lastname: Kersten
authors.forename: Klaus
authors.initials: K
authors.lastname: Harms
authors.forename: Gerhard
authors.initials: G
authors.lastname: Hilt
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002073:Butanes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000880:Anthraquinones; D002073:Butanes; D011090:Polyenes; C000599112:kwanzoquinone A; D003035:Cobalt; C436724:2,3-dimethyl-1,3-butadiene