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Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of cis-β-Lactones

Authors

  • Dr. Weiwu Ren,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Yichao Bian,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Ziyang Zhang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Dr. Hai Shang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Pengtao Zhang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Yuejie Chen,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Prof. Dr. Zhen Yang,

    Corresponding author
    1. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871 (China)
    • Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871 (China)
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  • Dr. Tuoping Luo,

    Corresponding author
    1. H3 Biomedicine Inc., 300 Technology Square, Cambridge, MA 02139 (USA)
    • H3 Biomedicine Inc., 300 Technology Square, Cambridge, MA 02139 (USA)
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  • Prof. Dr. Yefeng Tang

    Corresponding author
    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
    • The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • We acknowledge the financial support from the National Science of Foundation of China (20832003), China’s 985 project (411307141), and New Teachers’ Fund for Doctor Stations, Ministry of Education (20110002120011) to Y.T. T.L. is grateful to Prof. Stuart L. Schreiber (Harvard University) for the inspiring education.

Abstract

original image

Let's swap: A scalable, atom-economic, enantio-, and diastereoselective synthetic route to trisubstituted γ-butyrolactones based on a Wagner–Meerwein-type dyotropic rearrangement of cis-β-lactones is described (see scheme). This methodology was applied in efficient and protecting-group-free formal syntheses and total syntheses of various xanthanolide natural products.

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