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<p><i>Securinega</i> alkaloids constitute a structurally diverse class of natural products with intriguing architectures and biological activities. Herein, we report the discovery of four new <i>Securinega</i> alkaloids, flueggeacosines D–F and securingine J, from <i>Flueggea suffruticosa</i>. Flueggeacosines D and E possess dimeric frameworks incorporating a benzoquinolizidine motif derived from allosecurinine backbone. A concise synthetic strategy combining TBADT-catalyzed radical hydroacylation and Mo(CO)<sub>6</sub>-mediated reductive rearrangement enables efficient access to these complex alkaloids. Our synthetic approach also realizes a synthesis-based natural product anticipation predicting and confirming the existence of flueggeacosine F and securingine J in <i>F. suffruticosa</i>. Furthermore, oxidative rearrangements of flueggeacosine A furnish flueggeacosines D and F, supporting a plausible biosynthetic linkage. These findings establish a unified route to oxidized dimeric <i>Securinega</i> alkaloids and demonstrate the synergy of synthesis and biosynthetic reasoning in natural product discovery.</p>

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Discovery and synthesis of flueggeacosines D–F and securingine J

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月13日

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  • Chungwoo Lee,
  • Si Hyeon Chae,
  • Gyumin Kang,
  • Eric Jaewon Lee,
  • Ki Hyun Kim,
  • Sunkyu Han

摘要

Securinega alkaloids constitute a structurally diverse class of natural products with intriguing architectures and biological activities. Herein, we report the discovery of four new Securinega alkaloids, flueggeacosines D–F and securingine J, from Flueggea suffruticosa. Flueggeacosines D and E possess dimeric frameworks incorporating a benzoquinolizidine motif derived from allosecurinine backbone. A concise synthetic strategy combining TBADT-catalyzed radical hydroacylation and Mo(CO)6-mediated reductive rearrangement enables efficient access to these complex alkaloids. Our synthetic approach also realizes a synthesis-based natural product anticipation predicting and confirming the existence of flueggeacosine F and securingine J in F. suffruticosa. Furthermore, oxidative rearrangements of flueggeacosine A furnish flueggeacosines D and F, supporting a plausible biosynthetic linkage. These findings establish a unified route to oxidized dimeric Securinega alkaloids and demonstrate the synergy of synthesis and biosynthetic reasoning in natural product discovery.