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Synthesis of Tri‑, Tetra‑, and Pentacarbonyl Derivatives via Ozonolysis of 1,4-Dienes and Cyclization to Polyaromatic Systems

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journal contribution
posted on 05.12.2014, 00:00 by Laura Kersten, Klaus Harms, Gerhard Hilt
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.