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<p>Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature.</p>

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Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年1月2日

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  • Yunxia Yang,
  • Dong Xie,
  • Liang Huo,
  • Yue Liu,
  • Jinbo Duan,
  • Huilin Li,
  • Pan-Pan Zhou,
  • Xingang Xie,
  • Xuegong She

摘要

Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature.