SIOC English
有机化学
高级检索

有机化学 >

2025 , Vol. 45 >Issue 3: 725 - 747

DOI: https://doi.org/10.6023/cjoc202408029

综述与进展

四奎烷及类四奎烷全合成研究进展

  • 杨云博 ,
  • 丁寒锋
展开
  • 浙江大学化学系 杭州 310058

收稿日期: 2024-08-26

  修回日期: 2024-10-06

  网络出版日期: 2024-11-28

基金资助

国家自然科学基金(22125109); 国家自然科学基金(22371250); 浙江省自然科学基金(LZ22B020002); 中央高校基本科研业务费(226-2024-00003)

收起

Advances in the Total Syntheses of Tetraquinane and Tetraquinane-Type Terpenes

  • Yunbo Yang ,
  • Hanfeng Ding
Expand
  • Department of Chemistry, Zhejiang University, Hangzhou 310058
*

Received date: 2024-08-26

  Revised date: 2024-10-06

  Online published: 2024-11-28

Supported by

National Natural Science Foundation of China(22125109); National Natural Science Foundation of China(22371250); Zhejiang Provincial Natural Science Foundation of China(LZ22B020002); Fundamental Research Funds for the Central Universities(226-2024-00003)

Fold

摘要

多奎烷是指结构上由两个以上环戊烷通过并环方式形成碳骨架的一类天然产物, 其独特的化学结构和潜在的生物活性引起了合成化学家的广泛兴趣. 其中, 具有四个五元全碳环稠合而成的四奎烷以及由三个五元全碳环及一个六元全碳环稠合而成的类四奎烷在结构上最为独特. 本综述按照时间顺序依次总结、介绍四奎烷及类四奎烷的全合成研究进展.

关键词： 天然产物; 多奎烷; 四奎烷; 类四奎烷; 全合成

本文引用格式

杨云博 , 丁寒锋 . 四奎烷及类四奎烷全合成研究进展[J]. 有机化学, 2025 , 45(3) : 725 -747 . DOI: 10.6023/cjoc202408029

Abstract

Polyquinane is a class of natural products composed of multiple fused five-membered carbocycles. Their unique structures and potential biological activities have attracted the interest of the synthetic community. Among them, the structures with four fused five-membered carbocycles (known as tetraquinane), and those with three five-membered carbocycles fused by one six-membered carbocycle that referred to as tetraquinane-type terpenes, are particularly distinctive. This review provides a chronological overview of the total synthesis efforts of tetraquinane and tetraquinane-type terpenes.

Key words： nature products; polyquinane; tetraquinane; tetraquinane-type terpenes; total synthesis

参考文献

[1]
(a) Li, H.; Zhang, J.; She, X. Chem.-Eur. J. 2021, 27, 4839.
[1]
(b) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671.
[2]
(a) Chen, X.; Yao, W.; Zheng, H.; Wang, H.; Zhou, P.-P.; Zhu, D.-Y.; Wang, S.-H. J. Am. Chem. Soc. 2023, 145, 13549.
[2]
(b) Sun, D.; Chen, R.; Tang, D.; Xia, Q.; Zhao, Y.; Liu, C.-H.; Ding, H. J. Am. Chem. Soc. 2023, 145, 11927.
[2]
(c) Wang, Y.; Yang, C.; Huang, S.-H. Chin. J. Org. Chem. 2024, 44, 1371. (in Chinese)
[2]
(汪洋, 杨晨, 黄莎华, 有机化学, 2024, 44, 1371.)
[3]
Xue, Y.; Hou, S.-H.; Zhang, X.; Zhang, F.-M.; Zhang, X.-M.; Tu, Y.-Q. J. Am. Chem. Soc. 2024, 146, 25445.
[4]
Xu, K.; Mu, S.; Rao, H.; Hu, J.; Ding, H. Angew. Chem., Int. Ed. 2023, 62, e202303668.
[5]
(a) Anke, T.; Heim, J.; Knoch, F.; Mocek, U.; Steffan, B.; Steglich, W. Angew. Chem., Int. Ed. 1985, 24, 709.
[5]
(b) Han, J. W.; Oh, M.; Lee, Y. J.; Choi, J.; Choi, G. J.; Kim, H. Molecules 2018, 23, 2377.
[6]
Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
[7]
(a) Kang, T.; Song, S. B.; Kim, W.-Y.; Kim, B. G.; Lee, H.-Y. J. Am. Chem. Soc. 2014, 136, 10274.
[7]
(b) Yao, L.; Gui, J. Chin. J. Org. Chem. 2022, 42, 2703. (in Chinese)
[7]
(姚良才, 桂敬汉, 有机化学, 2022, 42, 2703.)
[8]
Hossain, M. L.; Ye, F.; Zhang, Y.; Wang, J. J. Org. Chem. 2013, 78, 1236.
[9]
Huang, Z.; Huang, J.; Qu, Y.; Zhang, W.; Gong, J.; Yang, Z. Angew. Chem., Int. Ed. 2018, 57, 8744.
[10]
(a) Zhao, Y.; Hu, J.; Chen, R.; Xiong, F.; Xie, H.; Ding, H. J. Am. Chem. Soc. 2022, 144, 2495.
[10]
(b) Gao, K.; Hu, J.; Ding, H. Acc. Chem. Res. 2021, 54, 875.
[10]
(c) Liu, Z.; Hu, J.; Ding, H. Org. Lett. 2021, 23, 6745.
[10]
(d) Wang, B.; Liu, Z.; Tong, Z.; Gao, B.; Ding, H. Angew. Chem., Int. Ed. 2021, 60, 14892.
[10]
(e) Hu, J.; Jia, Z.; Xu, K.; Ding, H. Org. Lett. 2020, 22, 1426.
[10]
(f) Gao, J.; Rao, P.; Xu, K.; Wang, S.; Wu, Y.; He, C.; Ding, H. J. Am. Chem. Soc. 2020, 142, 4592.
[10]
(g) He, C.; Bai, Z.; Hu, J.; Wang, B.; Xie, H.; Yu, L.; Ding, H. Chem. Commun. 2017, 53, 8435.
[10]
(h) He, C.; Hu, J.; Wu, Y.; Ding, H. J. Am. Chem. Soc. 2017, 139, 6098.
[11]
Xu, B.; Zhang, Z.; Tantillo, D. J.; Dai, M. J. Am. Chem. Soc. 2024.
[12]
Kozikowski, A. P.; Jung, S. H. J. Org. Chem. 1986, 51, 3400.
[13]
Liu, M.; Sun, W.; Shen, L.; He, Y.; Liu, J.; Wang, J.; Hu, Z.; Zhang, Y. Angew. Chem., Int. Ed. 2019, 58, 12091.
[14]
Li, B.; Tan, C.; Ma, T.; Jia, Y. Angew. Chem., Int. Ed. 2024, 63, e202319306.
[15]
Sun, S.; Wei, Q.; Liu, Y.; Lu, Z. J. Am. Chem. Soc. 2024, 146, 14427.
[16]
Hayashi, Y.; Gotoh, H.; Honma, M.; Sankar, K.; Kumar, I.; Ishikawa, H.; Konno, K.; Yui, H.; Tsuzuki, S.; Uchimaru, T. J. Am. Chem. Soc. 2011, 133, 20175.
[17]
Roncal, T.; Cordobés, S.; Sterner, O.; Ugalde, U. Eukaryotic Cell 2002, 1, 823.
[18]
Hou, S.-H.; Tu, Y.-Q.; Wang, S.-H.; Xi, C.-C.; Zhang, F.-M.; Wang, S.-H.; Li, Y.-T.; Liu, L. Angew. Chem., Int. Ed. 2016, 55, 4456.
[19]
Hu, P.; Chi, H. M.; DeBacker, K. C.; Gong, X.; Keim, J. H.; Hsu, I. T.; Snyder, S. A. Nature 2019, 569, 703.
[20]
Xu, B.; Xun, W.; Su, S.; Zhai, H. Angew. Chem., Int. Ed. 2020, 59, 16475.
[21]
Kim, J.; Lee, S.; Han, S.; Lee, H.-Y. Chem 2023, 9, 1270.
[22]
Clarke, D. B.; Hinkley, S. F. R.; Weavers, R. T. Tetrahedron Lett. 1997, 38, 4297.
[23]
Xin, Z.; Wang, H.; He, H.; Gao, S. Tetrahedron Lett. 2021, 71.
[24]
Lee, H.; Kang, T.; Lee, H.-Y. Angew. Chem.,Int. Ed. 2017, 56, 8254.
[25]
Qu, Y.; Wang, Z.; Zhang, Z.; Zhang, W.; Huang, J.; Yang, Z. J. Am. Chem. Soc. 2020, 142, 6511.
[26]
(a) Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 1097.
[26]
(b) Bleschke, C.; Tissot, M.; Mueller, D.; Alexakis, A. Org. Lett. 2013, 15, 2152.
[27]
Peng, C.; Arya, P.; Zhou, Z.; Snyder, S. A. Angew. Chem., Int. Ed. 2020, 59, 13521.
[28]
May, T. L.; Brown, M. K.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2008, 47, 7358.
[29]
Rosenbaum, L.-C.; Haefner, M.; Gaich, T. Angew. Chem., Int. Ed. 2021, 60, 2939.
[30]
Wang, Y.-P.; Fang, K.; Tu, Y.-Q.; Yin, J.-J.; Zhao, Q.; Ke, T. Nat. Commun. 2022, 13, 2335.
[31]
Rodriguez, I. I.; Rodriguez, A. D.; Zhao, H. J. Org. Chem. 2009, 74, 7581.
[32]
Amberg, W. M.; Carreira, E. M. J. Am. Chem. Soc. 2022.
[33]
Lemiere, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207.
[34]
Wang, Y.; Su, Y. J.; Jia, Y. X. J. Am. Chem. Soc. 2023, 145, 9459.
[35]
Toyomasu, T.; Kaneko, A.; Tokiwano, T.; Kanno, Y.; Kanno, Y.; Niida, R.; Miura, S.; Nishioka, T.; Ikeda, C.; Mitsuhashi, W.; Dairi, T.; Kawano, O.; Oikawa, H.; Kato, N.; Sassa, T. J. Org. Chem. 2009, 74, 1541.
[36]
Yin, J.-J.; Wang, Y.-P.; Xue, J.; Zhou, F.-F.; Shan, X.-Q.; Zhu, R.; Fang, K.; Shi, L.; Zhang, S.-Y.; Hou, S.-H.; Xia, W.-J.; Tu, Y. Q. J. Am. Chem. Soc. 2023, 145, 21170.
[37]
Fang, K.; Dou, B.-H.; Zhang, F.-M.; Wang, Y.-P.; Shan, Z.-R.; Wang, X.-Y.; Hou, S.-H.; Tu, Y.; Ding, T.-M. Angew. Chem., Int. Ed. 2024, e202412337.
Options
文章导航

/

〈 〉