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Total Synthesis of (−)-Jiadifenin

Authors

  • Dr. Yang Yang,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Dr. Xingnian Fu,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Dr. Jianwei Chen,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Prof. Dr. Hongbin Zhai

    Corresponding author
    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
    • Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • We thank the National Basic Research Program of China (973 Program: 2010CB833200),the NSFC (21172100), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT: IRT1138), and “111” Program of MOE for financial support.

Abstract

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As easy as ABCD: (−)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4′-bromo-2′-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland–Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson–Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.

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