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2025 , Vol. 45 >Issue 3: 1030 - 1039

DOI: https://doi.org/10.6023/cjoc202406024

研究论文

保护基效应对几类天然产物全合成的影响

  • 易九州 ,
  • 火亮 ,
  • 陈金燕 ,
  • 刘勐 ,
  • 李辉林 ,
  • 厍学功
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  • 兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000

收稿日期: 2024-06-18

  修回日期: 2024-08-01

  网络出版日期: 2024-09-19

基金资助

国家自然科学基金(22231003); 国家自然科学基金(22071090); 国家自然科学基金(22171115)

收起

Protecting Group Effects on the Total Syntheses of Several Classes of Natural Products

  • Jiuzhou Yi ,
  • Liang Huo ,
  • Jinyan Chen ,
  • Meng Liu ,
  • Huilin Li ,
  • Xuegong She
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  • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
* E-mail: ;

Received date: 2024-06-18

  Revised date: 2024-08-01

  Online published: 2024-09-19

Supported by

National Natural Science Foundation of China(22231003); National Natural Science Foundation of China(22071090); National Natural Science Foundation of China(22171115)

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摘要

保护基的合理选择对天然产物全合成具有重要的影响. 通过几类天然产物的全合成研究发现, 保护基不仅具有屏蔽活性官能团反应性的作用, 还会对反应过程和合成路线带来多方面影响, 包括导致分子骨架重排、参与预期的反应生成副产物以及影响立体中心构型的控制等. 针对此, 结合近期完成的天然产物全合成的研究案例, 分析了具体情况下如何处理保护基效应带来的影响, 提出了不同的解决方案包括更换保护基、直接应用保护基带来的副产物以及放弃使用保护基等. 这三种方案成功解决了合成中的保护基问题, 为成功实现目标天然产物的全合成奠定了重要基础.

关键词： 保护基; 天然产物; 全合成; 骨架重排; 副反应

本文引用格式

易九州 , 火亮 , 陈金燕 , 刘勐 , 李辉林 , 厍学功 . 保护基效应对几类天然产物全合成的影响[J]. 有机化学, 2025 , 45(3) : 1030 -1039 . DOI: 10.6023/cjoc202406024

Abstract

The proper utilization of protecting groups plays a pivotal role in the total synethesis of natural products. Recently, in the research on the total synthesis of several polycyclic natural products, it was found that, besides the masking effect on active functional groups, protecting groups brought many other effects to the chemical reactions and route evaluations of the synthesis in the following aspects including leading to unexpected skeletal rearrangement or reorganization, participating the designed reaction to produce unexpected byproducts, and affecting the outcome of stereoselectivity. In response to this, based on recent research cases on the complete synthesis of natural products, how to deal with the impact of protective group effects in specific situations is analyzed, and different solutions including replacing protective groups, directly applying by-products from protective groups, and abandoning the use of protective groups are proposed. These three solutions successfully tackled the probelms in the synthesis, and laid the foundation of final success on the total synthesis of the target molecules.

Key words： protecting group; natural product; total synthesis; skeletal rearrangement; side reaction

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