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Total Synthesis of Kingianins A, D, and F

Authors

  • Samuel L. Drew,

    1. Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200 (Australia)
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  • Dr. Andrew L. Lawrence,

    Corresponding author
    1. Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200 (Australia)
    • Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200 (Australia)
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  • Prof. Michael S. Sherburn

    Corresponding author
    1. Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200 (Australia)
    • Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200 (Australia)
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  • This work was supported by the Australian Research Council. A.L.L. gratefully acknowledges financial support from the Australian Research Council in the form of a Discovery Early Career Researcher Award (DE120102113). S.L.D. gratefully acknowledges financial support from the Rickards family through the Rodney Rickards Scholarship. We thank Prof. Litaudon (CNRS, France) for kindly providing copies of the original NMR data. We also thank Mr. Tony Herlt (ANU) for assistance with HPLC and Mr. Chris Blake (ANU) for NMR measurements.

Abstract

original image

Schlüsselschritte der Totalsynthese von (±)-Kingianin A, D und F sind die partielle Reduktion eines konjugierten Tetrains zu (Z,Z,Z,Z)-Tetraen, der Domino-8π-6π-elektrocyclische Ringschluss des (Z,Z,Z,Z)-Tetraens und die durch ein Radikalkation katalysierte formale Diels-Alder-Dimerisierung eines funktionalisierten Bicyclo[4.2.0]octadiens.

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