Asymmetric Synthesis and Biosynthetic Implications of (+)-Fusarisetin A

Authors

  • Jun Yin,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
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    • These authors contributed equally to this work.

  • Cheng Wang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
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    • These authors contributed equally to this work.

  • Lili Kong,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
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  • Shujun Cai,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
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  • Prof. Dr. Shuanhu Gao

    Corresponding author
    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
    • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China)
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  • Financial support was provided by the “Yingcai Program” of East China Normal University, the NSFC (21102045), and the Shanghai “Pujiang Program” (11PJ1402800).

Abstract

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Starting from equisetin, the asymmetric synthesis of (+)-fusarisetin A has been accomplished in a one-pot transformation including a biomimetic oxidation and an intramolecular Diels–Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.

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