Chinese Journal of Organic Chemistry >
Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid
Received date: 2021-05-28
Revised date: 2021-07-15
Online published: 2021-08-19
Supported by
National Key Research and Development Program of China(2016YFA0602900); National Natural Science Foundation of China(21672110); National Natural Science Foundation of China(21925105); Natural Science Foundation of Tianjin City(18JCJQJC47000)
Schisandraceae is widely spread within our country. As a kind of traditional Chinese herb, it is known for its anti-hepatitis bioactivity. The diversified and unique structures in this family have drawn the attention of many synthetic chemists. The recent efforts towards the total synthesis of schisandra triterpenoid are summarized.
Key words： schisandraceae; schisandra triterpenoid; total synthesis
Lu Guo , Pingping Tang . Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 3816 -3825 . DOI: 10.6023/cjoc202105049
| [1] | Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871. |
| [2] | Shi, Y. M.; Xiao, W. L.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2015, 32, 367. |
| [3] | Tang, Y.; Zhang, Y.; Dai, M.; Luo, T.; Deng, L.; Chen, J.; Yang, Z. Org. Lett. 2005, 7, 885. |
| [4] | Hui, Y. Z. Comprehensive Natural Products in Tradational Chinese Medicine, Shanghai Scientific and Technical Publishers, Shanghai, 2011. (in Chinese) |
| [4] | (惠永正, 中药天然产物大全, 上海科学技术出版社, 上海, 2011.) |
| [5] | Li, R. T.; Zhao, Q. S.; Li, S. H.; Han, Q. Bin; Sun, H. D.; Lu, Y.; Zhang, L. L.; Zheng, Q. T. Org. Lett. 2003, 5, 1023. |
| [6] | Zhang, Y. D.; Tang, Y. F.; Luo, T. P.; Shen, J.; Chen, J. H.; Yang, Z. Org. Lett. 2006, 8, 107. |
| [7] | Zhang, Y. D.; Ren, W. W.; Lan, Y.; Xiao, Q.; Wang, K.; Xu, J.; Chen, J. H.; Yang, Z. Org. Lett. 2008, 10, 665. |
| [8] | Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345. |
| [9] | Fischer, D.; Theodorakis, E. A. Eur. J. Org. Chem. 2007, 25, 4193. |
| [10] | Wang, Q.; Chen, C. Org. Lett. 2008, 10, 1223. |
| [11] | Paquette, L. A.; Kwong, W. L. Org. Lett. 2008, 10, 2111. |
| [12] | Kwong, W. L.; Paquette, L. A. Org. Lett. 2008, 10, 2115. |
| [13] | Paquette, L. A.; Lai, K. W. Org. Lett. 2008, 10, 3781. |
| [14] | Cordonnier, M. C. A.; Jennifer Kan, S. B.; Anderson, E. A. Chem. Commun. 2008, 44, 5818. |
| [15] | Goh, S. S.; Baars, H.; Gockel, B.; Anderson, E. A. Org. Lett. 2012, 14, 6278. |
| [16] | Gockel, B.; Goh, S. S.; Puttock, E. J.; Baars, H.; Chaubet, G.; Anderson, E. A. Org. Lett. 2014, 16, 4480. |
| [17] | Mehta, G.; Bhat, A. B.; Kumara, T. H. S. Tetrahedron Lett. 2009, 50, 6597. |
| [18] | Mehta, G.; Bhat, B. A.; Suresha Kumara, T. H. Tetrahedron Lett. 2010, 51, 4069. |
| [19] | Mehta, G.; Bhat, B. A. Tetrahedron Lett. 2009, 50, 2474. |
| [20] | Mehta, G.; Yaragorla, S. A. Tetrahedron Lett. 2013, 54, 549. |
| [21] | Matcha, K.; Maity, S.; Malik, C. K.; Ghosh, S. Tetrahedron Lett. 2010, 51, 2754. |
| [22] | Maity, S.; Matcha, K.; Ghosh, S. J. Org. Chem. 2010, 75, 4192. |
| [23] | Hossain, M. F.; Matcha, K.; Ghosh, S. Tetrahedron Lett. 2011, 52, 6473. |
| [24] | Bartoli, A.; Chouraqui, G.; Parrain, J. L. Org. Lett. 2012, 14, 122. |
| [25] | Peng, Y.; Duan, S. M.; Wang, Y. W. Tetrahedron Lett. 2015, 56, 4509. |
| [26] | Wang, Y.; Li, Z.; Lv, L.; Xie, Z. Org. Lett. 2016, 18, 792. |
| [27] | Wang, Y.; Zhang, Y.; Li, Z.; Yang, Z.; Xie, Z. Org. Chem. Front. 2017, 4, 47. |
| [28] | Werner, B.; Kalesse, M. Org. Lett. 2017, 19, 1524. |
| [29] | Sun, T. W.; Ren, W. W.; Xiao, Q.; Tang, Y. F.; Zhang, Y. D.; Li, Y.; Meng, F. K.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2321. |
| [30] | Li, Y.; Chen, Z. X.; Xiao, Q.; Ye, Q. D.; Sun, T. W.; Meng, F. K.; Ren, W. W.; You, L.; Xu, L. M.; Wang, Y. F.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2334. |
| [31] | Ren, W. W.; Chen, Z. X.; Xiao, Q.; Li, Y.; Sun, T. W.; Zhang, Z. Y.; Ye, Q. D.; Meng, F. K.; You, L.; Zhao, M. Z.; Xu, L. M.; Tang, Y. F.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2341. |
| [32] | Xiao, Q.; Ren, W. W.; Chen, Z. X.; Sun, T. W.; Li, Y.; Ye, Q. D.; Gong, J. X.; Meng, F. K.; You, L.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Shan, Z. H.; Shi, Y.; Tang, Y. F.; Chen, J. H.; Yang, Z. Angew. Chem., nt. Ed. 2011, 50, 7373. |
| [33] | You, L.; Liang, X. T.; Xu, L. M.; Wang, Y. F.; Zhang, J. J.; Su, Q.; Li, Y. H.; Zhang, B.; Yang, S. L.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2015, 137, 10120. |
| [34] | Han, Y. X.; Jiang, Y. L.; Li, Y.; Yu, H. X.; Tong, B. Q.; Niu, Z.; Zhou, S. J.; Liu, S.; Lan, Y.; Chen, J. H.; Yang, Z. Nat. Commun. 2017, 8, 1. |
| [35] | Liu, D. D.; Sun, T. W.; Wang, K. Y.; Lu, Y.; Zhang, S. L.; Li, Y. H.; Jiang, Y. L.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 5732. |
| [36] | Jiang, Y. L.; Yu, H. X.; Li, Y.; Qu, P.; Han, Y. X.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2020, 142, 573. |
| [37] | Wang, Y.; Chen, B.; He, X.; Gui, J. J. Am. Chem. Soc. 2020, 142, 5007. |
| [38] | Wang, Y.; Chen, B.; He, X.; Gui, J. Chin. J. Chem. 2020, 38, 1339. |
| [39] | Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 20, 8. |
| [40] | Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew. Chem., nt. Ed. 2016, 55, 6964. |
| [41] | Goh, S. S.; Chaubet, G.; Gockel, B.; Cordonnier, M.-C. A.; Baars, H.; Phillips, A. W.; Anderson, E. A. Angew. Chem., Int. Ed. 2015, 54, 12618. |
| [42] | Mohammad, M.; Chintalapudi, V.; Carney, J. M.; Mansfield, S. J.; Sanderson, P.; Christensen, K. E.; Anderson, E. A. Angew. Chem., nt. Ed. 2019, 58, 18177. |
| [43] | Ma, B.; Zhao, Y.; He, C.; Ding, H. Angew. Chem., nt. Ed. 2018, 57, 15567. |
| [44] | Wang, H.; Zhang, X.; Tang, P. Chem. Sci. 2017, 8, 7246. |
| [45] | Wang, H.; Wang, L.; Li, Y.; Zhang, X.; Tang, P. Chin. J. Chem. 2019, 37, 255. |
| [46] | Wang, L.; Wang, H.; Li, Y.; Tang, P. Angew. Chem., nt. Ed. 2015, 54, 5732. |
| [47] | Li, X.; Cheong, P. H. Y.; Carter, R. G. Angew. Chem., nt. Ed. 2017, 56, 1704. |
| [48] | Yan, B.; Hu, K.; Sun, H.; Puno, P. Chin. J. Org. Chem. 2018, 38, 2259. (in Chinese) |
| [48] | (颜秉超, 胡坤, 孙汉董, 普诺•白玛丹增, 有机化学, 2018, 38, 2259.) |
| [49] | Yang, Z. Acc. Chem. Res. 2019, 52, 480. |
| [50] | Bhat, B. A.; Rashid, S.; Sengupta, S.; Mehta, G. Asian J. Org. Chem. 2020, 9, 449. |
| [51] | Fu, S.; Liu, B. Org. Chem. Front. 2020, 7, 1903. |
| [52] | Meng, F. Y.; Sun, J. X.; Li, X.; Yu, H. Y.; Li, S. M.; Ruan, H. L. Org. Lett. 2011, 13, 1502. |
| [53] | Xiao, W. L.; Yang, L. M.; Gong, N. B.; Wu, L.; Wang, R. R.; Pu, J. X.; Li, X. L.; Huang, S. X.; Zheng, Y. T.; Li, R. T.; Lu, Y.; Zheng, Q. T.; Sun, H. D. Org. Lett. 2006, 8, 991. |
| [54] | Yang, P.; Li, J.; Sun, L.; Yao, M.; Zhang, X.; Xiao, W. L.; Wang, J. H.; Tian, P.; Sun, H. D.; Puno, P. T.; Li, A. J. Am. Chem. Soc. 2020, 142, 13701. |
| [55] | Lei, C.; Xiao, W. L.; Huang, S. X.; Chen, J. J.; Pu, J. X.; Sun, H. D. Tetrahedron 2010, 66, 2306. |
| [56] | Lei, C.; Huang, S. X.; Chen, J. J.; Yang, L. Bin; Xiao, W. L.; Chang, Y.; Lu, Y.; Huang, H.; Pu, J. X.; Sun, H. D. J. Nat. Prod. 2008, 71, 1228. |
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