综述与进展

多卤代海洋来源天然产物全合成

  • 杨庆星 ,
  • 刘璇 ,
  • 马硕 ,
  • 李欣欣 ,
  • 马东旭 ,
  • 徐涛
展开
  • a 中国海洋大学医药学院 海洋药物教育部重点实验室 功能分子合成与应用青岛市重点实验室 山东青岛 266071
    b 青岛海洋科技中心 海洋药物与生物制品功能实验室 山东青岛 266237

收稿日期: 2024-08-30

  修回日期: 2024-10-01

  网络出版日期: 2024-11-20

基金资助

国家自然科学优秀青年基金(82122063)

Total Syntheses of Marine-Derived Polyhalogenated Natural Products

  • Qingxing Yang ,
  • Xuan Liu ,
  • Shuo Ma ,
  • Xinxin Li ,
  • Dongxu Ma ,
  • Tao Xu
Expand
  • a Molecular Synthesis Center, Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266071
    b Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao, Shandong 266237

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)

摘要

卤素掺入是海洋生物用于修饰其多用途代谢物的一种独特策略, 通常会导致生物活性以及体内代谢或降解历程的改变. 同时, 卤素的引入也会增加海洋天然产物结构的复杂性及其鉴定难度. 近年来多卤取代的海洋来源天然产物独特的化学结构与多样性的生物学功能引起了有机合成化学家的广泛兴趣. 此综述将从多卤吲哚生物碱(Caulamidines, Perophoramidine, Hinckdentine A, Spiroindimicins, Dictazole B, Securiflustra securifrons, Nortopsentin D)、其它多卤生物碱(Psammaplysins, Massadine, Axinellamine, Discorhabdins)和典型多卤甾体天然产物(Clionastatins)三个方面总结近年来多卤取代的海洋来源天然产物全合成的研究进展.

本文引用格式

杨庆星 , 刘璇 , 马硕 , 李欣欣 , 马东旭 , 徐涛 . 多卤代海洋来源天然产物全合成[J]. 有机化学, 2025 , 45(3) : 764 -803 . DOI: 10.6023/cjoc202408037

Abstract

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.

参考文献

[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.
文章导航

/