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2025 , Vol. 45 >Issue 3: 881 - 895

DOI: https://doi.org/10.6023/cjoc202408012

综述与进展

二萜生物碱全合成研究进展

  • 李闯 ,
  • 张成 ,
  • 刘小宇 ,
  • 秦勇
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  • 四川大学华西药学院 成都 610041

收稿日期: 2024-08-08

  修回日期: 2024-09-29

  网络出版日期: 2024-11-20

基金资助

国家自然科学基金(22071161)

收起

Recent Progress in the Total Synthesis of Diterpenoid Alkaloids

  • Chuang Li ,
  • Cheng Zhang ,
  • Xiaoyu Liu ,
  • Yong Qin
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  • West China School of Pharmacy, Sichuan University, Chengdu 610041
* E-mail: ;

Received date: 2024-08-08

  Revised date: 2024-09-29

  Online published: 2024-11-20

Supported by

National Natural Science Foundation of China(22071161)

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摘要

二萜生物碱是一类具有复杂化学结构和丰富生物活性的天然产物. 长期以来, 二萜生物碱独特的笼状骨架、多立体手性中心和稠密的含氧取代基团使其成为天然产物全合成领域的挑战性目标分子. 近五年, 该领域的研究取得了显著进展. 综述了2020年至今报道的二萜生物碱全合成工作, 重点介绍创新合成方法和策略的发展与应用.

关键词： 二萜生物碱; 天然产物; 全合成; 合成方法与策略

本文引用格式

李闯 , 张成 , 刘小宇 , 秦勇 . 二萜生物碱全合成研究进展[J]. 有机化学, 2025 , 45(3) : 881 -895 . DOI: 10.6023/cjoc202408012

Abstract

Diterpenoid alkaloids are a family of natural products with complex chemical structures and a rich array of biological activities. Their unique cage-like skeletons, multiple stereogenic chiral centers, and densely oxygenated substituents have long rendered them challenging target molecules in the field of total synthesis of natural product. In the past five years, significant progress has been made in this research area. The total synthesis of diterpenoid alkaloids reported from 2020 to the present is reviewed, focusing on the development and application of innovative synthetic methods and strategies.

Key words： diterpenoid alkaloid; natural product; total synthesis; synthetic method and strategy

参考文献

[1]
Liu, X.-Y.; Ke, B.; Qin, Y.; Wang, F.-P. Chemistry and Biology, In The Alkaloids: Chemistry and Biology, Vol. 87, Ed.: Knölker, H.-J., Elsevier, New York, 2022, pp. 1-360.
[2]
Wang, F.-P.; Chen, Q.-H.; Liu, X.-Y. Nat. Prod. Rep. 2010, 27, 529.
[3]
Shen, Y.; Liang, W.-J.; Shi, Y.-N.; Kennelly, E. J.; Zhao, D.-K. Nat. Prod. Rep. 2020, 37, 763.
[4]
Cherney, E. C.; Baran, P. S. Isr. J. Chem. 2011, 51, 391.
[5]
Zhu, G.; Liu, R.; Liu, B. Synthesis 2015, 47, 2691.
[6]
Liu, X.-Y.; Qin, Y. Nat. Prod. Rep. 2017, 34, 1044.
[7]
Dank, C.; Sanichar, R.; Choo, K.-L.; Olsen, M.; Lautens, M. Synthesis 2019, 51, 3915.
[8]
Doering, N. A.; Sarpong, R.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2020, 59, 10722.
[9]
McCowen, S. V.; Doering, N. A.; Sarpong, R. Chem. Sci. 2020, 11, 7538.
[10]
Liu, X.-Y.; Wang, F.-P.; Qin, Y. Acc. Chem. Res. 2021, 54, 22.
[11]
Wiesner, K.; Ho, P.; Tsai, C. S. J.; Lam, Y. Can. J. Chem. 1974, 52, 2355.
[12]
Sethi, S. P.; Atwal, K. S.; Marini-Bettolo, R. M.; Tsai, T. Y. R.; Wiesner, K. Can. J. Chem. 1980, 58, 1889.
[13]
Huang, H.-X.; Mi, F.; Li, C.; He, H.; Wang, F.-P.; Liu, X.-Y.; Qin, Y. Angew. Chem., Int. Ed. 2020, 59, 23609.
[14]
Boeckman, R. K. Jr.; Biegasiewicz, K. F.; Tusch, D. J.; Miller, J. R. J. Org. Chem. 2015, 80, 4030.
[15]
Jin, S.; Zhao, X.; Ma, D. J. Am. Chem. Soc. 2022, 144, 15355.
[16]
Liu, Y.; Liniger, M.; McFadden, R. M.; Roizen, J. L.; Malette, J.; Reeves, C. M.; Behenna, D. C.; Seto, M.; Kim, J.; Mohr, J. T.; Virgil, S. C.; Stoltz, B. M. Beilstein J. Org. Chem. 2014, 10, 2501.
[17]
Taber, D. F.; Liang, J.-L.; Chen, B.; Cai, L. J. Org. Chem. 2005, 70, 8739.
[18]
Hamlin, A. M.; de Jesus Cortez, F.; Lapointe, D.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 4854.
[19]
Cherney, E. C.; Lopchuk, J. M.; Green, J. C.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 12592.
[20]
Li, X.-H.; Zhu, M.; Wang, Z.-X.; Liu, X.-Y.; Song, H.; Zhang, D.; Wang, F.-P.; Qin, Y. Angew. Chem., Int. Ed. 2016, 55, 15667.
[21]
Liu, J.; Ma, D.-W. Angew. Chem., Int. Ed. 2018, 57, 6676.
[22]
Zhou, S.; Guo, R.; Yang, P.; Li, A. J. Am. Chem. Soc. 2018, 140, 9025.
[23]
Zhang, Q.; Zhang, Z.; Huang, Z.; Zhang, C.; Xi, S.; Zhang, M. Angew. Chem., Int. Ed. 2018, 57, 937.
[24]
Zhang, Q.; Yang, Z.; Wang, Q.; Liu, S.; Zhou, T.; Zhao, Y.; Zhang, M. J. Am. Chem. Soc. 2021, 143, 7088.
[25]
Muratake, H.; Natsume, M. Angew. Chem., Int. Ed. 2004, 43, 4646.
[26]
Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734.
[27]
Peese, K. M.; Gin, D. Y. Chem. Eur. J. 2008, 14, 1654.
[28]
Kou, K. G. M.; Pflueger, J. J.; Kiho, T.; Morrill, L. C.; Fisher, E. L.; Clagg, K.; Lebold, T. P.; Kisunzu, J. K.; Sarpong, R. J. Am. Chem. Soc. 2018, 140, 8105.
[29]
Yu, K.; Yao, F.; Zeng, Q.; Xie, H.; Ding, H. J. Am. Chem. Soc. 2021, 143, 10576.
[30]
Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226.
[31]
Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500.
[32]
Masamune, S. J. Am. Chem. Soc. 1964, 86, 290.
[33]
Nagata, W.; Narisada, M.; Wakabayashi, T.; Sugasawa, T. J. Am. Chem. Soc. 1964, 86, 929.
[34]
Valenta, Z.; Wiesner, K.; Wong, C. M. Tetrahedron Lett. 1964, 5, 2437.
[35]
Nagata, W.; Narisada, M.; Wakabayashi, T.; Sugasawa, T. J. Am. Chem. Soc. 1967, 89, 1499.
[36]
Li, C.; Lu, F.; Cai, Y.; Zhang, C.; Shao, Y.; Zhang, Y.; Liu, X.-Y.; Qin, Y. J. Am. Chem. Soc. 2024, 146, 1081.
[37]
Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
[38]
Hong, B.; Liu, W.; Wang, J.; Wu, J.; Kadonaga, Y.; Cai, P.; Lou, H.; Yu, Z.; Li, H.; Lei, X. Chem 2019, 5, 1671.
[39]
Wu, J.; Kadonaga, Y.; Hong, B.; Wang, J.; Lei, X. Angew. Chem., Int. Ed. 2019, 58, 10879.
[40]
Prein, M.; Adam, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 477.
[41]
Wiesner, K.; Tsai, T. Y. R.; Huber, K.; Bolton, S. E.; Vlahov, R. J. Am. Chem. Soc. 1974, 96, 4990.
[42]
Shi, Y.; Wilmot, J. T.; Nordstrøm, L. U.; Tan, D. S.; Gin, D. Y. J. Am. Chem. Soc. 2013, 135,14313.
[43]
Marth, C. J.; Gallego, G. M.; Lee, J. C.; Lebold, T. P.; Kulyk, S.; Kou, K. G. M.; Qin, J.; Lilien, R.; Sarpong, R. Nature 2015, 528, 493.
[44]
Kou, K. G. M.; Kulyk, S.; Marth, C. J.; Lee, J. C.; Doering, N. A.; Li, B. X.; Gallego, G. M.; Lebold, T. P.; Sarpong, R. J. Am. Chem. Soc. 2017, 139,13882.
[45]
Nishiyama, Y.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2016, 18, 2359.
[46]
Nishiyama, Y.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2017, 19, 5833.
[47]
Kamakura, D.; Todoroki, H.; Urabe, D.; Hagiwara, K.; Inoue, M. Angew. Chem., Int. Ed. 2020, 59, 479.
[48]
Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963.
[49]
Fleming, I.; Henning, R.; Parker, D. C.; Parker, H. E.; Plaut, P. E.; Sanderson, J. J. Chem. Soc., Perkin Trans. 1. 1 1995, 317.
[50]
Subba Reddy, B. V.; Nair, P. N.; Antony, A.; Lalli, C.; Grée, R. Eur. J. Org. Chem. 2017, 1805.
[51]
Wong, A. R.; Fastuca, N. J.; Mak, V. W.; Kerkovius, J. K.; Stevenson, S. M.; Reisman, S. E. ACS Cent. Sci. 2021, 7, 1311.
[52]
Hagiya, K.; Yamasaki, A.; Okuyama, T.; Sugimura, T. Tetrahedron: Asymmetry 2004, 15, 1409.
[53]
Sugimura, T.; Yamasaki, A.; Okuyama, T. Tetrahedron: Asymmetry 2005, 16, 675.
[54]
Liu, Z.-G.; Cheng, H.; Ge, M.-J.; Xu, L.; Wang, F.-P. Tetrahedron 2013, 69, 5431.
[55]
Shimakawa, T.; Nakamura, S.; Asai, H.; Hagiwara, K.; Inoue, M. J. Am. Chem. Soc. 2023, 145, 600.
[56]
Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
[57]
Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
[58]
Xiong, J.; Tan, N.-H.; Ji, C.-J.; Lu, Y.; Gong, N.-B. Tetrahedron Lett. 2008, 49, 4851.
[59]
Ji, J.; Chen, J.; Qin, S.; Li, W.; Zhao, J.; Li, G.; Song, H.; Liu, X. Y.; Qin, Y. J. Am. Chem. Soc. 2023, 145, 3903.
[60]
Smaligo, A. J.; Swain, M.; Quintana, J. C.; Tan, M. F.; Kim, D. A.; Kwon, O. Science 2019, 364, 681.
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