Chinese Journal of Organic Chemistry >
Research on the Biomimetic Construction of Propeller-Shaped Dual Lactone Ring System in Cephalotanin B
Received date: 2024-08-25
Revised date: 2024-09-24
Online published: 2024-11-20
Supported by
National Natural Science Foundation of China(21772153); National Natural Science Foundation of China(22071192); Shaanxi Fundamental Science Research Project for Chemistry and Biology(23JHZ003); Science and Technology Department of Shaanxi Province(2019JM-151)
As a member of the family of Cephalotaxus diterpenoids, cephalotanin B possesses a quite unique propeller-shaped dual lactone ring system. Based on known proposal of biosynthetic pathway, two biomimetic construction approaches were explored successively, a novel epoxide-opening/elimination/dual lactonization cascade was exploited, and a brief and efficient biomimetic construction strategy for the unique propeller-shaped dual lactone ring system was developed successfully in the end.
Key words： natural product; complex structure; biomimetic synthesis
Zezhong Sun , Shuang Jin , Yunxia Wang , Xiangdong Hu . Research on the Biomimetic Construction of Propeller-Shaped Dual Lactone Ring System in Cephalotanin B[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 996 -1002 . DOI: 10.6023/cjoc202408028
| [1] | Buta, J. G.; Flippen, J. L.; Lusby, W. R. J. Org. Chem. 1978, 43, 1002. |
| [2] | Sun, N.-J.; Xue, Z.; Liang, X.-T.; Huang, L. Acta Pharm. Sin. 1979, 14, 39. |
| [3] | Du, J.; Chiu, M.-H.; Nie, R.-L. J. Nat. Prod. 1999, 62, 1664. |
| [4] | Yoon, K. D.; Jeong, D. G.; Hwang, Y. H.; Ryu, J. M.; Kim, J. J. Nat. Prod. 2007, 70, 2029. |
| [5] | He, Y.-R.; Shen, Y.-H.; Shan, L.; Yang, X.; Wen, B.; Ye, J.; Yuan, X.; Li, H.-L.; Xu, X.-K.; Zhang, W.-D. RSC Adv. 2015, 5, 4126. |
| [6] | Ni, G.; Zhang, H.; Fan, Y.-Y.; Liu, H.-C.; Ding, J.; Yue, J.-M. Org. Lett. 2016, 18, 1880. |
| [7] | Xu, J.-B.; Fan, Y.-Y.; Gan, L.-S.; Zhou, Y.-B.; Li, J.; Yue, J.-M. Chem.-Eur. J. 2016, 22, 14648. |
| [8] | Zhao, J.-X.; Fan, Y.-Y.; Xu, J.-B.; Gan, L.-S.; Xu, C.-H.; Ding, J.; Yue, J.-M. J. Nat. Prod. 2017, 80, 356. |
| [9] | Fan, Y.-Y.; Xu, J.-B.; Liu, H.-C.; Gan, L.-S.; Ding, J.; Yue, J.-M. J. Nat. Prod. 2017, 80, 3159. |
| [10] | Ni, L.; Zhong, X.-H.; Chen, X.-J.; Zhang, B.-J.; Bao, M.-F.; Cai, X.-H. Phytochemistry 2018, 151, 50. |
| [11] | Ge, Z.-P.; Liu, H.-C.; Wang, G.-C.; Liu, Q.-F.; Xu, C.-H.; Ding, J.; Fan, Y.-Y.; Yue, J.-M. J. Nat. Prod. 2019, 82, 1565. |
| [12] | Zhao, C.-X.; Li, B.-Q.; Shao, Z.-X.; Li, D.-H.; Jing, Y.-K.; Li, Z.-L.; Hua, H.-M. Tetrahedron Lett. 2019, 60, 151154. |
| [13] | Li, Y.; Wang, Y.; Shao, Z.; Zhao, C.; Jing, Q.; Li, D.; Lin, B.; Jing, Y.; Li, Z.; Hua, H. Bioorg. Chem. 2020, 103, 104226. |
| [14] | Huang, Q.-P.; Guo, K.; Liu, Y.; Liu, Y.-C.; Li, W.-Y.; Geng, H.; Wang, Y.; Li, S.-H. Chem. Biodiversity 2020, 17, e2000210. |
| [15] | Ge, Z.-P.; Fan, Y.-Y.; Deng, W.-D.; Zheng, C.-Y.; Li, T.; Yue, J.-M. Angew. Chem., Int. Ed. 2021, 60, 9374. |
| [16] | Jiang, C.; Xue, J.; Yuan, Y.; Li, Y.; Zhao, C.; Jing, Q.; Zhang, X.; Yang, M.; Han, T.; Bai, J.; Li, Z.; Li, D.; Hua, H. Phytochemistry 2021, 192, 112939. |
| [17] | Ge, Z.-P.; Zhou, B.; Zimbres, F. M.; Cassera, M. B.; Zhao, J.-X.; Yue, J.-M. Chin. J. Chem. 2022, 40, 1177. |
| [18] | Ge, Z.-P.; Zhou, B.; Zimbres, F. M.; Haney, R. S.; Liu, Q.-F.; Wu, Y.; Cassera, M. B.; Zhao, J.-X.; Yue, J.-M. Org. Biomol. Chem. 2022, 20, 9000. |
| [19] | Jiang, C.; Han, Z.; Sun, W.; Tan, J.; Gao, G.; Wang, X.; Hua, H.; Zhao, R.; Han, T. Phytochemistry 2024, 217, 113924. |
| [20] | Ge, Z.-P.; Xu, J.-B.; Zhao, P.; Xiang, M.; Zhou, Y.; Lin, Z.-M.; Zuo, J.-P.; Zhao, J.-X.; Yue, J.-M. Phytochemistry 2024, 221, 114038. |
| [21] | Zhao, J.-X.; Ge, Z.-P.; Yue, J.-M. Nat. Prod. Rep. 2024, 41, 1152. |
| [22] | Sasse, J. M.; Rowan, K. S.; Galbraith, M. N. Phytochemistry 1981, 20, 2195. |
| [23] | Kang, S.; Cai, S.; Teng, L. Acta Pharm. Sin. 1981, 16, 867. |
| [24] | Sun, N.-J.; Xue, Z.; Liang, X.-T.; Huang, L. Acta Pharm. Sin. 1982, 17, 236. |
| [25] | Han, J. J. Ethnopharmacol. 1988, 24, 1. |
| [26] | Mei, W.-L.; Wu, J.; Dai, H.-F. Chin. Tradit. Herb. Drugs 2006, 37, 452. (in Chinese) |
| [26] | (梅文莉, 吴娇, 戴好富, 中草药, 2006, 37, 452.) |
| [27] | Evanno, L.; Jossang, A.; Nguyen-Pouplin, J.; Delaroche, D.; Herson, P.; Seuleiman, M.; Bodo, B.; Nay, B. Planta Med. 2008, 74, 870. |
| [28] | Rogers, D. H.; Morris, J. C.; Roden, F. S.; Frey, B.; King, G. R.; Russkamp, F.-W.; Bell, R. A.; Mander, L. N. Pure Appl. Chem. 1996, 68, 515. |
| [29] | Frey, B.; Wells, A. P.; Rogers, D. H.; Mander, L. N. J. Am. Chem. Soc. 1998, 120, 1914. |
| [30] | Zhang, M.; Liu, N.; Tang, W. J. Am. Chem. Soc. 2013, 135, 12434. |
| [31] | Zhang, H.-J.; Hu, L.; Ma, Z.; Li, R.; Zhang, Z.; Tao, C.; Cheng, B.; Li, Y.; Wang, H.; Zhai, H. Angew. Chem., Int. Ed. 2016, 55, 11638. |
| [32] | Xu, L.; Wang, C.; Gao, Z.; Zhao, Y.-M. J. Am. Chem. Soc. 2018, 140, 5653. |
| [33] | Zhang, H.; He, H.; Gao, S. Angew. Chem., Int. Ed. 2020, 59, 20417. |
| [34] | Zhang, H.; He, H.; Gao, S. Org. Chem. Front. 2021, 8, 555. |
| [35] | Haider, M.; Sennari, G.; Eggert, A.; Sarpong, R. J. Am. Chem. Soc. 2021, 143, 2710. |
| [36] | Ren, Z.; Sun, Z.; Li, Y.; Fan, X.; Dai, M.; Wang, Y.; Hu, X. Angew. Chem., Int. Ed. 2021, 60, 18572. |
| [37] | Ao, Q.; Zhang, H.-J.; Zheng, J.; Chen, X.; Zhai, H. Angew. Chem., Int. Ed. 2021, 60, 21267. |
| [38] | Lu, Y.; Xu, M.-M.; Zhang, Z.-M.; Zhang, J.; Cai, Q. Angew. Chem., Int. Ed. 2021, 60, 26610. |
| [39] | Li, A.; He, Z.; Liu, B.; Yang, Z.; Zhang, Z. Org. Lett. 2021, 23, 9237. |
| [40] | Qing, Z.; Mao, P.; Wang, T.; Zhai, H. J. Am. Chem. Soc. 2022, 144, 10640. |
| [41] | Sennari, G.; Gardner, K. E.; Wiesler, S.; Haider, M.; Eggert, A.; Sarpong R. J. Am. Chem. Soc. 2022, 144, 19173. |
| [42] | Sun, Z.; Fan, X.; Sun, Z.; Li, Z.; Niu, L.; Guo, H.; Ren, Z.; Wang, Y.; Hu, X. Org. Lett. 2022, 24, 7507. |
| [43] | Wang, H.; Liu, Y.; Zhang, H.; Yang, B.; He, H.; Gao, S. J. Am. Chem. Soc. 2023, 145, 16988. |
| [44] | Sun, Z.; Jin, S.; Song, J.; Niu, L.; Zhang, F.; Gong, H.; Shu, X.; Wang, Y.; Hu, X. Angew. Chem., Int. Ed. 2023, 62, e202312599. |
| [45] | Shao, H.; Ma, Z.-H.; Cheng, Y.-Y.; Guo, X.-F.; Sun, Y.-K.; Liu, W.-J.; Zhao, Y.-M. Angew. Chem., Int. Ed. 2024, 63, e202402931. |
| [46] | Wiesler, S.; Sennari, G.; Popescu, M. V.; Gardner, K. E.; Aida, K.; Paton, R. S.; Sarpong, R. Nat. Commun. 2024, 15, 4125. |
| [47] | Zhang, Z.-A.; Gan, X.-C.; Tian, G.; Shi, X.-Y.; Qin, C.; Wang, J. ChemRxiv 2024, doi:10.26434/chemrxiv-2024-rp8s5. |
| [48] | Fang, X.; Zhang, N.; Chen, S.-C.; Luo, T. J. Am. Chem. Soc. 2022, 144, 2292. |
| [49] | Zhao, Y.; Hu, J.; Chen, R.; Xiong, F.; Xie, H.; Ding, H. J. Am. Chem. Soc. 2022, 144, 2495. |
| [50] | Cui, H.; Shen, Y.; Chen, Y.; Wang, R.; Wei, H.; Fu, P.; Lei, X.; Wang, H.; Bi, R.; Zhang, Y. J. Am. Chem. Soc. 2022, 144, 8938. |
| [51] | Shu, X.; Chen, C.-C.; Yu, T.; Yang, J.; Hu, X. Angew. Chem., Int. Ed. 2021, 60, 18514. |
| [52] | Bickley, J. F.; Roberts, S. M.; Santoro, M. G.; Snape, T. J. Tetrahedron 2004, 60, 2569. |
| [53] | Posner, G. H.; Lee, S. H. T.; Kim, H. J.; Peleg, S.; Dolan, P.; Kensler, T. W. Bioorg. Med. Chem. 2005, 13, 2959. |
| [54] | Ouyang, X.-Y.; Jiang, H.-F.; Huang, J.-M. Chin. J. Chem. 2006, 24, 1480. |
/
| 〈 |
|
〉 |
