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Gram Scale Synthesis of (±)-Gregatin A via 1, 3-dipolar Cycloaddition Strategy
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  • Yiming Ding,
  • Xiaoli Zhao,
  • Chunlei Qu,
  • Xianwen Long,
  • Yaqiu Zhao,
  • Xiao-Dong Yang,
  • Haixiang Shen,
  • Jun Deng
Yiming Ding
Yunnan University
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Xiaoli Zhao
Yunnan University
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Chunlei Qu
Nankai University
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Xianwen Long
Nankai University
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Yaqiu Zhao
China Academy of Chinese Medical Sciences
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Xiao-Dong Yang
Yunnan University
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Haixiang Shen
Wuwei Occupational College
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Jun Deng
Nankai University

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Abstract

Here, we present a 6-step gram-scale synthesis of (±)-gregatin A, a fungal polyketide characterized by an alkylated furanone core origi-nally isolated from Cephalosporium gregatum. The synthetic route features an intermolecular 1,3-dipolar cycloaddition, a Mo-mediated disconnection of isoxazole skeleton, and an acid-mediated desilylation/enamine hydrolysis and hemiketalization cascade. Notably, this synthetic approach establishes a versatile platform applicable to the synthesis of diverse gregatin congeners, allowing for the introduc-tion of varied side chains. Our method not only facilitates the scalable production of (±)-gregatin A but also opens avenues for the ex-ploration of structural analogs with unique biological activities.
Submitted to Chinese Journal of Chemistry
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26 Jun 2024Review(s) Completed, Editorial Evaluation Pending