REVIEWS

Recent Progress in the Total Synthesis of Diterpenoid Alkaloids

  • Chuang Li ,
  • Cheng Zhang ,
  • Xiaoyu Liu ,
  • Yong Qin
Expand
  • West China School of Pharmacy, Sichuan University, Chengdu 610041

Received date: 2024-08-08

  Revised date: 2024-09-29

  Online published: 2024-11-20

Supported by

National Natural Science Foundation of China(22071161)

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.

Cite this article

Chuang Li , Cheng Zhang , Xiaoyu Liu , Yong Qin . Recent Progress in the Total Synthesis of Diterpenoid Alkaloids[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 881 -895 . DOI: 10.6023/cjoc202408012

References

[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.
Outlines

/