Chinese Journal of Organic Chemistry >
Total Syntheses of Marine-Derived Polyhalogenated Natural Products
Received date: 2024-08-30
Revised date: 2024-10-01
Online published: 2024-11-20
Supported by
National Natural Science Foundation of China for Excellent Young Scholars(82122063)
The incorporation of halogens is a unique strategy employed by marine organisms to modify their multifunctional metabolites, often leading to changes in biological activity and the metabolic or degradation processes in vivo. At the same time, the introduction of halogens increases the structural complexity of marine natural products, making their identification more challenging. In recent years, the unique chemical structures and diverse biological functions of polyhalogenated marine-derived natural products have garnered significant interest from organic synthetic chemists. Recent advances in the total synthesis of polyhalogenated marine-derived natural products, focusing on polyhalogenated indole alkaloids (Caulamidines, Perophoramidine, Hinckdentine A, Spiroindimicins, Dictazole B, Securiflustra securifrons, Nortopsentin D), other polyhalogenated alkaloids (Psammaplysins, Massadine, Axinellamine, Discorhabdins), and representative polyhalogenated steroidal natural products (Clionastatins) are summarized.
Qingxing Yang , Xuan Liu , Shuo Ma , Xinxin Li , Dongxu Ma , Tao Xu . Total Syntheses of Marine-Derived Polyhalogenated Natural Products[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 764 -803 . DOI: 10.6023/cjoc202408037
| [1] | Agarwal, V.; Miles, Z. D.; Winter, J. M.; Eustaquio, A. S.; El Gamal, A. A.; Moore, B. S. Chem. Rev. 2017, 117, 5619. |
| [2] | Chung, W.-J.; Vanderwal, C. D. Angew. Chem.,Int. Ed. 2016, 55, 4396. |
| [3] | Dvorak, K. R.; Tepe, J. J. Nat. Prod. Rep. 2024, 41, 1264. |
| [4] | Singh, N.; Singh, S.; Kohli, S.; Singh, A.; Asiki, H.; Rathee, G.; Chandra, R.; Anderson, E. A. Org. Chem. Front. 2021, 8, 5550. |
| [5] | Milanowski, D. J.; Oku, N.; Cartner, L. K.; Milanowski, D. J.; Oku, N.; Cartner, L. K.; Bokesch, H. R.; Williamson, R. T.; Saurí, J.; Liu, Y.; Blinov, K. A.; Ding, Y.; Li, X.-C.; Ferreira, D.; Walker, L. A.; Khan, S.; Davies-Coleman, M. T.; Kelley, J. A.; McMahon, J. B.; Martin, G. E.; Gustafson, K. R. Chem. Sci. 2018, 9, 307. |
| [6] | Tian, X. R.; Wang, D.; Jiang, W.; Bokesch, H. R.; Wilson, B. A.; O’Keefe, B. R.; Gustafson, K. R. J. Nat. Prod. 2023, 86, 1855. |
| [7] | Zhu, Z.; Maimone, T. J. J. Am. Chem. Soc. 2023, 145, 14215. |
| [8] | Yu, H. Y.; Zhang, J. H.; Ma, D. X.; Li, X. T.; Xu, T. J. Am. Chem. Soc. 2023, 145, 22335. |
| [9] | Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124. |
| [10] | Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068. |
| [11] | Wu, H. X.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052. |
| [12] | Zhang, H. L.; Hong, L.; Kang, H.; Wang, R. J. Am. Chem. Soc. 2013, 135, 14098. |
| [13] | Trost, B. M.; Osipov, M.; Krügera, S.; Zhang, Y. Chem. Sci. 2015, 6, 349. |
| [14] | Han, S.-J.; Vogt, F.; Krishnan, S.; May, J. A.; Gatti, M.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2014, 16, 3316. |
| [15] | Blackman, A. J.; Hambley, T. W.; Picker, K.; Taylor, W. C.; Thirasasana, N. Tetrahedron Lett. 1987, 28, 5561. |
| [16] | Higuchi, K.; Sato, Y.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Org. Lett. 2009, 11, 197. |
| [17] | Douki, K.; Ono, H.; Taniguchi, T.; Shimokawa, J.; Kitamura, M.; Fukuyama, T. J. Am. Chem. Soc. 2016, 138, 14578. |
| [18] | Torres-Ochoa, R. O.; Buyck, T.; Wang, Q.; Zhu, J. P. Angew. Chem., Int. Ed. 2018, 57, 5679. |
| [19] | Hou, Z. W.; Yan, H.; Song, J. S.; Xu, H. C. Chin. J. Chem. 2018, 36, 909. |
| [20] | Jeon, J.; Lee, S. E.; Cheon, C.-H. Org. Lett. 2021, 23, 2169. |
| [21] | Ruan, Z. W.; Wang, M.; Yang, C.; Zhu, L. L.; Su, Z. S.; Hong, R. JACS Au 2022, 2, 793. |
| [22] | Ruan, Z. W.; Zhu, L. L.; Zheng, K..; Hong, R. Tetrahedron Lett. 2021, 67, 152880. |
| [23] | Baidilov, D.; Elkin, P. K.; Athe, S.; Rawal, V. H. J. Am. Chem. Soc. 2023, 145, 14831. |
| [24] | Blair, L. M.; Sperry, J. Chem. Commun. 2016, 52, 800. |
| [25] | Zhang, Z.; Ray, S.; Imlay, L.; Callaghan, L. T.; Niederstrasser, H.; Mallipeddi, P. L.; Posner, B. A.; Wetzel, D. M.; Phillips, M. A.; Smith, M. W. Chem. Sci. 2021, 12, 10388. |
| [26] | Zheng, X. K.; Li, Y.; Guan, M.; Wang, L. Y.; Wei, S. L.; Li, Y.-C.; Chang, C.-Y.; Xu, Z. R. Angew. Chem., Int. Ed. 2022, 61, e202208802. |
| [27] | Banerjee, A.; Brisco, T. A.; Zhang, Z.; Busse, A. A.; Sumida, K.; Smith, M. W. Org. Lett. 2023, 25, 8413. |
| [28] | Bialonska, D.; Zjawiony, J. K. Mar. Drugs 2009, 7, 166. |
| [29] | Kazlauskas, R.; Murphy, P. T.; Quinn, R. J.; Wells, R. J. Tetrahedron Lett. 1977, 1, 61. |
| [30] | Skiredj, A.; Beniddir, M. A.; Joseph, D.; Leblanc, K.; Bernadat, G.; Evanno, L.; Poupon, E. Angew. Chem., Int. Ed. 2014, 53, 6419. |
| [31] | Duchemin, N.; Skiredj, A.; Mansot, J.; Leblanc, K.; Vasseur, J.-J.; Beniddir, M. A.; Evanno, L.; Poupon, E.; Smietana, M.; Arseniyadis, S. Angew. Chem., Int. Ed. 2018, 57, 11786. |
| [32] | Anthoni, U.; Chevolot, L.; Larsen, C.; Nielsen, P. H.; Christophersen, C. J. Org. Chem. 1987, 52, 4709. |
| [33] | Rahbaek, L.; Anthoni, U.; Christophersen, C.; Nielsen, P. H.; Petersen, B. O. J. Org. Chem. 1996, 61, 887. |
| [34] | Baran, P. S.; Shenvi, R. A. J. Am. Chem. Soc. 2006, 128, 14028. |
| [35] | Alexander, B. W.; Bartfield, N. M.; Gupta, V.; Mercado, B. Q.; Campo, M. D.; Herzon, S. B. Scienc 2024, 383, 849. |
| [36] | Mancini, I.; Guella, G.; Pietra, F.; Debitus, C.; Waikedre, J. Helv. Chim. Acta 1996, 79, 2075. |
| [37] | Keel, K. L.; Tepe, J. J. Org. Lett. 2021, 23, 5368. |
| [38] | Morrow, A. P.; Smith, M. W. J. Am. Chem. Soc. 2024, 146, 2913. |
| [39] | Paciorek, J.; Höfler, D.; Sokol, K. R.; Wurst, K.; Magauer, T. J. Am. Chem. Soc. 2022, 144, 19704. |
| [40] | Zhang, L.; Wang, R.; Wang, C.; Liu, B.; Yang, J.; Zhang, Z.; Huang, J.; Yang, Z. Org. Lett. 2022, 24, 3786. |
| [41] | (a) Yamaguchi, J.; Seiple, I. B.; Young, I. S.; Malley, D. P.; Maue, M.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 3578. |
| [41] | (b) Su, S.; Seiple, I. B.; Young, I. S.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 16490. |
| [42] | Ma, Z.-Q.; Wang, X.-L.; Wang, X.; Rodriguez, R. A.; Moore, C. E.; Gao, S.-H.; Tan, X.-H.; Ma, Y.-Y.; Rheingold, A. L.; Chuo, C.; Baran, P. S.; Rheingold, A. L. Science 2014, 346, 219. |
| [43] | Su, S.; Rodriguez, R. A.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 13922. |
| [44] | Ma, Z.-Q.; Wang, X.; Ma, Y.-Y.; Chuo, C. Angew. Chem., Int. Ed. 2016, 55, 4763. |
| [45] | Goey, A. K. L.; Chau, C. H.; Sissung, T. M.; Cook, K. M.; Venzon, D. J.; Castro, A.; Ransom, T. R.; Henrich, C. J.; McKee, T. C.; McMahon, J. B.; Grkovic, T.; Cadelis, M. M.; Copp, B. R.; Gustafson, K. R.; Figg, W. D. J. Nat. Prod. 2016, 79, 1267. |
| [46] | Nishiyama, S.; Cheng, J. F.; Tao, X. L.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4151. |
| [47] | Tao, X. L.; Cheng, J. F.; Nishiyama, S.; Yamamura, S. Tetrahedron 1994, 50, 2017. |
| [48] | Cheng, J. F.; Nishiyama, S.; Yamamura, S. Chem. Lett. 1990, 19, 1591. |
| [49] | Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175. |
| [50] | Aubart, K. M.; Heathcock, C. H. J. Org. Chem. 1999, 64, 16. |
| [51] | Tohma, H.; Harayama, Y.; Hashizume, M.; Iwata, M.; Egi, M.; Kita, Y. Angew. Chem., Int. Ed. 2002, 41, 348. |
| [52] | Tohma, H.; Harayama, Y.; Hashizume, M.; Iwata, M.; Egi, M.; Kita, Y.; Kiyono, M. J. Am. Chem. Soc. 2003, 125, 11235. |
| [53] | Shimomura, M.; Ide, K.; Sakata, J.; Tokuyama, H. J. Am. Chem. Soc. 2023, 145, 18233. |
| [54] | Derstine, B. C.; Cook, A. J.; Collings, J. D.; Gair, J.; Saurí, J.; Kwan, E. E.; Burns, N. Z. Angew. Chem., Int. Ed. 2024, 63, e202315284. |
| [55] | Ju, W.; Wang, X.-D.; Tian, H.-L.; Gui, J.-H. J. Am. Chem. Soc. 2021, 143, 13016. |
| [56] | Cui, H.; Shen, Y.; Chen, Y.-Y.; Wang, R.-F.; Wei, H.-X.; Fu, P.-F.; Lei, X.; Wang, H.-X.; Bi, R.-H.; Zhang, Y.-D. J. Am. Chem. Soc. 2022, 144, 8938. |
/
| 〈 |
|
〉 |
