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Total Synthesis of Rhizopodin

Authors

  • Dipl.-Chem. Michael Dieckmann,

    1. Universität Heidelberg, Organisch-Chemisches Institut, INF 270, 69120 Heidelberg (Germany)
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    • These authors contributed equally to this work.

  • Dipl.-Chem. Manuel Kretschmer,

    1. Universität Heidelberg, Organisch-Chemisches Institut, INF 270, 69120 Heidelberg (Germany)
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    • These authors contributed equally to this work.

  • Dr. Pengfei Li,

    1. Universität Heidelberg, Organisch-Chemisches Institut, INF 270, 69120 Heidelberg (Germany)
    2. Present address: Xi'an Jiaotong University, Xi'an, Shaanxi Province (PR China)
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  • Dr. Sven Rudolph,

    1. Universität Heidelberg, Organisch-Chemisches Institut, INF 270, 69120 Heidelberg (Germany)
    2. Present address: ASM Research Chemicals, Hannover (Germany)
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  • Dipl.-Chem. Daniel Herkommer,

    1. Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn (Germany)
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  • Prof. Dr. Dirk Menche

    Corresponding author
    1. Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn (Germany)
    • Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn (Germany)
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  • We thank the DFG (Me 2756/4-1), the DFG Graduiertenkolleg 850 (scholarship to M.K. and M.D.), the “Fonds der Chemischen Industrie”, and the “Wild-Stiftung” for generous funding, and Wiebke Ahlbrecht, Johannes Troendlin, Carolin Lang, and Nathalie-Desirée Costa Pinheiro for exploratory studies. Excellent assistance with NMR analyses by Prof. Markus Enders and Beate Termin is gratefully acknowledged. We thank Prof. Günter Helmchen for helpful discussions and assistance with HPLC analyses.

Abstract

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Symmetry helps: The total synthesis of the potent actin-targeting C2-symmetric myxobacterial macrolide rhizopodin (see scheme) is accomplished by the convergent assembly of three building blocks of similar complexity, a concise macrocyclization strategy, and a late-stage introduction of the labile side chains.

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