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<p>Kopsane alkaloids possess a complex heptacyclic scaffold and exhibit significant biological activities, including cholinergic, anti-inflammatory, and anti-cancer effects. While we previously reported PtCl<sub>2</sub>-catalyzed [3 + 2] cycloaddition for their synthesis, the high cost and toxicity of platinum necessitate sustainable alternatives. In this study, we employed density functional theory (DFT) to investigate MCl<sub>2</sub> (M = Ni, Pd, and Pt) catalyzed [3 + 2] cycloaddition in Kopsane alkaloid synthesis. Our results indicate consistent reaction characteristics across all metals, with the second cyclization acting as the diastereoselectivity-determining step. The calculated energy gaps between transition states (TS2s) for NiCl<sub>2</sub>, PdCl<sub>2</sub>, and PtCl<sub>2</sub> were 5.57, 1.45, and 12.25 kcal/mol, respectively. These energy profiles suggest that NiCl<sub>2</sub> can achieve high diastereoselectivity similar to PtCl<sub>2</sub> due to its significant energy gap (&gt; 4 kcal/mol). The implementation of this computational chemistry technique provides theoretical evidence that could help to improve the efficiency of the catalyst designing process.</p><p></p>

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Exploring NiCl2, PdCl2 and PtCl2 as a catalyst for [3 + 2] cycloaddition in Kopsane alkaloid synthesis by density functional theory study

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月21日

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  • Sanghee Yoon,
  • Pratanphorn Nakliang,
  • Bilal Shaker,
  • Tao Ye,
  • Sun Choi

摘要

Kopsane alkaloids possess a complex heptacyclic scaffold and exhibit significant biological activities, including cholinergic, anti-inflammatory, and anti-cancer effects. While we previously reported PtCl2-catalyzed [3 + 2] cycloaddition for their synthesis, the high cost and toxicity of platinum necessitate sustainable alternatives. In this study, we employed density functional theory (DFT) to investigate MCl2 (M = Ni, Pd, and Pt) catalyzed [3 + 2] cycloaddition in Kopsane alkaloid synthesis. Our results indicate consistent reaction characteristics across all metals, with the second cyclization acting as the diastereoselectivity-determining step. The calculated energy gaps between transition states (TS2s) for NiCl2, PdCl2, and PtCl2 were 5.57, 1.45, and 12.25 kcal/mol, respectively. These energy profiles suggest that NiCl2 can achieve high diastereoselectivity similar to PtCl2 due to its significant energy gap (> 4 kcal/mol). The implementation of this computational chemistry technique provides theoretical evidence that could help to improve the efficiency of the catalyst designing process.