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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

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A synthesis fit for a king: The total synthesis of (±)-kingianins A, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π–6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels–Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.

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