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2020 , Vol. 40 >Issue 11: 3536 - 3558

DOI: https://doi.org/10.6023/cjoc202010025

综述与进展

过渡金属催化环加成反应合成八元碳环研究进展(2010~2020)

  • 王路宁 ,
  • 余志祥
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  • 北京大学化学与分子工程学院 北京分子科学国家研究中心 生物有机与分子工程教育部重点实验室 北京 100871

收稿日期: 2020-10-16

  修回日期: 2020-11-09

  网络出版日期: 2020-11-12

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Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Eight-Membered Carbocycles: an Update from 2010 to 2020

  • Wang Lu-Ning ,
  • Yu Zhi-Xiang
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  • Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871

Received date: 2020-10-16

  Revised date: 2020-11-09

  Online published: 2020-11-12

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摘要

八元碳环结构广泛存在于天然产物、药物分子（如紫杉醇和瑞他帕林）和香料分子等功能分子中.许多含有八元碳环的天然产物如vinigrol和ophiobolin（蛇孢假壳素）都显示出较好的生物活性.因此，合成这些含有八元碳环的分子将会为药物化学、化学生物学、香料化学、材料化学和其它科学的发展提供分子基础.八元碳环的合成一直是有机合成化学中的挑战之一.为了迎接这一挑战，许多卓有成就的化学家发展出了许多金属催化的环加成反应以合成八元碳环，从而为高效、原子经济性和步骤经济性地合成目标分子提供帮助.在2010年时，我们曾经对利用过渡金属催化的环加成反应制备八元碳环这一前沿方向进行过总结.本综述总结了2010~2020年期间该领域的最新进展，内容包括新型环加成反应的发展、环加成反应的应用以及机理研究，希望可以为关注此领域的有机化学家提供一定的启发和有益的指引，同时鼓励更多合成化学家利用这些环加成反应进行各种功能分子的合成，并发展出更多用于八元碳环合成的高效方法.

关键词： 八元碳环; 过渡金属催化; 环加成; 全合成

本文引用格式

王路宁 , 余志祥 . 过渡金属催化环加成反应合成八元碳环研究进展(2010~2020)[J]. 有机化学, 2020 , 40(11) : 3536 -3558 . DOI: 10.6023/cjoc202010025

Abstract

Eight-membered carbocycles are widely found in natural products with significant biological activities and other molecules ranging from perfumes to potential materials. Therefore, accessing these eight-membered carbocycle embedded molecules is important for drug discovery, biological investigation, fragrance industry, material development and many other fields. However, the synthesis of eight-membered carbocycles is still posing challenges to synthetic chemists. Hence, tremendous efforts have been endeavored by many leading chemists to discover and develop new reactions in order to synthesize eight-membered carbocycles. Among these reactions, transition-metal-catalyzed cycloadditions of [m+n], [m+n+o], [m+ n+o+p] have evolved as powerful tools to achieve this aim. This topic has been reviewed in 2010. Summarized here are many new developments in this field and applications of the previously developed reactions in natural product synthesis since then.

Key words： eight-membered carbocycles; transition metal catalysis; cycloaddition; total synthesis

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