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Total Synthesis of (±)-Pentalenolactone A Methyl Ester

Authors

  • Dr. Qi Liu,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Guozong Yue,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Na Wu,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Guang Lin,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Dr. Yuanzhen Li,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Prof. Dr. Junmin Quan,

    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Prof. Dr. Chuang-chuang Li,

    Corresponding author
    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
    • Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Dr. Guoxin Wang,

    Corresponding author
    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
    • Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • Prof. Dr. Zhen Yang

    Corresponding author
    1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
    2. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871 (China)
    • Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055 (China)
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  • We thank the 973 program (2012CB722602, 2010CB833201), and the National Science Foundation of China (20772002, 81161120401, 91013004) and the Shenzhen Basic Research Program (CXB201005260053A, JC201104210121A) for financial support.

Abstract

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Ringing it up: The methyl ester of pentalenolactone A has been obtained through the stereoselective synthesis of a cyclopentenone by a combination of the Co-mediated Pauson–Khand reaction (PKR) of enyne 1, and the construction of a quaternary-carbon-based strained α-methylidene-δ-pentyrolactone core through a trimethylsilyl (TMS) mediated, telescoped intramolecular Michael olefination (TIMO) reaction of keto-phosphonate 2.

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