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2025 , Vol. 45 >Issue 3: 925 - 932

DOI: https://doi.org/10.6023/cjoc202411005

研究论文

虎皮楠生物碱Daphniglaucin C的AB环系合成

  • 张晓锋 ,
  • Aggeliki Roumana ,
  • 毛海康 ,
  • 徐晶
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  • a 哈尔滨工业大学化学与化工学院 哈尔滨 150001
    b 南方科技大学化学系 深圳格拉布斯研究院 广东省催化化学重点实验室 深圳市小分子药物发现与合成重点实验室 广东深圳 518055

收稿日期: 2024-11-05

  修回日期: 2024-12-04

  网络出版日期: 2025-01-14

基金资助

国家自然科学基金(22271136); 国家自然科学基金(22471117)

收起

Synthesis of the AB Ring System of Daphniphyllum Alkaloid Daphniglaucin C

  • Xiaofeng Zhang ,
  • Aggeliki Roumana ,
  • Haikang Mao ,
  • Jing Xu
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  • a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
    b Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055
* E-mail: ;

Received date: 2024-11-05

  Revised date: 2024-12-04

  Online published: 2025-01-14

Supported by

National Natural Science Foundation of China(22271136); National Natural Science Foundation of China(22471117)

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摘要

从廉价易得的原料开始, 通过铑催化[4+3]环加成以及Heck偶联等关键反应, 高效简洁地得到了Daphniglaucin C虎皮楠生物碱的AB环系, 同时, 也尝试了利用黄氏酰胺活化增环反应进行C环构筑的探索. 本工作为Daphniglaucin C型虎皮楠生物碱的全合成提供了一条新的思路.

关键词： 虎皮楠生物碱; Daphniglaucin C; 铑催化环加成; Heck偶联; 全合成

本文引用格式

张晓锋 , Aggeliki Roumana , 毛海康 , 徐晶 . 虎皮楠生物碱Daphniglaucin C的AB环系合成[J]. 有机化学, 2025 , 45(3) : 925 -932 . DOI: 10.6023/cjoc202411005

Abstract

The AB ring system of Daphniphyllum alkaloid Daphniglaucin C was concisely synthesized from readily available starting materials through rhodium-catalyzed cyclization and Heck coupling. The formation of C-ring using Huang’s amide- activation-annulation was also investigated. This efficient strategy lays the foundation for the synthesis of Daphniglaucin C-type Daphniphyllum alkaloids.

Key words： Daphniphyllum alkaloid; Daphniglaucin C; Rh-catalyzed cycloaddition; Heck coupling; total synthesis

参考文献

[1]
Yagi, S. Kyoto Igaku Zasshi 1909, 6, 208.
[2]
(a) Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936.
[2]
(b) Li, Z.-Y.; Guo, Y.-W. Chin. J. Org. Chem. 2007, 27, 565. (in Chinese)
[2]
(李震宇, 郭跃伟, 有机化学, 2007, 27, 565.)
[2]
(c) Dong, M.; Zhang, M.-L.; Shi, Q.-W.; Gu, Y.-C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646.
[2]
(d) Yang, S.-P.; Yue, J.-M. Acta Pharmacol. Sin. 2012, 33, 1147.
[2]
(e) Wu, H.-F.; Zhang, X.-P.; Ding, L.-S.; Chen, S.-L.; Yang, J.-S.; Xu, X.-D. Planta Med. 2013, 79, 1589.
[3]
(a) Heathcock, C. H.; Davidsen, S. K.; Mills, S.; Sanner, M. A. J. Am. Chem. Soc. 1986, 108, 5650.
[3]
(b) Ruggeri, R. B.; Heathcock, C. H. J. Org. Chem. 1990, 55, 3714.
[3]
(c) Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120.
[3]
(d) Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734.
[3]
(e) Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532.
[3]
(f) Stafford, J. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5433.
[3]
(g) Ruggeri, R. B.; McClure, K. F.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 1530.
[3]
(h) Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575.
[4]
Weiss, M. E.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 11501.
[5]
(a) Lu, Z.; Li, Y.; Deng, J.; Li, A. Nat. Chem. 2013, 5, 679.
[5]
(b) Li, J.; Zhang, W.; Zhang, F.; Chen, Y.; Li, A. J. Am. Chem. Soc. 2017, 139, 14893.
[5]
(c) Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A. Angew. Chem., Int. Ed. 2018, 57, 952.
[5]
(d) Zhang, W.; Ding, M.; Li, J.; Guo, Z.; Lu, M.; Chen, Y.; Liu, L.; Shen, Y.-H.; Li, A. J. Am. Chem. Soc. 2018, 140, 4227.
[5]
(e) Zhang, W.; Lu, M.; Ren, L.; Zhang, X.; Liu, S.; Ba, M.; Yang, P.; Li, A. J. Am. Chem. Soc. 2023, 145, 26569.
[6]
(a) Shvartsbart, A.; Smith, A. B., III. J. Am. Chem. Soc. 2014, 136, 870.
[6]
(b) Shvartsbart, A.; Smith, A. B., III. J. Am. Chem. Soc. 2015, 137, 3510.
[7]
Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2016, 55, 6067.
[8]
(a) Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen, Q. N. N.; Paton, R. S.; Dixon, D. J. J. Am. Chem. Soc. 2017, 139, 17755.
[8]
(b) Kučera, R.; Ellis, S. R.; Yamazaki, K.; Cooke, J. H.; Chekshin, N.; Christensen, K. E.; Hamlin, T. A.; Dixon, D. J. J. Am. Chem. Soc. 2023, 145, 5422.
[9]
(a) Chen, X.; Zhang, H.-J.; Yang, X.; Lv, H.; Shao, X.; Tao, C.; Wang, H.; Cheng, B.; Li, Y.; Guo, J.; Zhang, J.; Zhai, H. Angew. Chem., Int. Ed. 2018, 57, 947.
[9]
(b) Su, S.; Lin, C.; Zhai, H. Angew. Chem., Int. Ed. 2023, 62, e202303402.
[10]
Xu, B.; Wang, B.-Y.; Xun, W.; Qiu, F. G. Angew. Chem., Int. Ed. 2019, 58, 5754.
[10]
(b) Wang, B.-Y.; Xu, B.; Xun, W.; Guo, Y.-M.; Zhang, J.; Qiu, F. G. Angew. Chem., Int. Ed. 2021, 60, 9439.
[11]
(a) Guo, L.-D.; Chen, Y.; Xu, J. Acc. Chem. Res. 2020, 53, 2726.
[11]
(b) Chen, Y.; Hu, J.; Guo, L.-D.; Zhong, W.; Ning, C.; Xu, J. Angew. Chem., Int. Ed. 2019, 58, 7390.
[11]
(c) Guo, L.-D.; Hou, J.; Tu, W.; Zhang, Y.; Zhang, Y.; Chen, L.; Xu, J. J. Am. Chem. Soc. 2019, 141, 11713.
[11]
(d) Guo, L.-D.; Hu, J.; Zhang, Y.; Tu, W.; Zhang, Y.; Pu, F.; Xu, J. J. Am. Chem. Soc. 2019, 141, 13043.
[11]
(e) Guo, L.-D.; Zhang, Y.; Hu, J.; Ning, C.; Fu, H.; Chen, Y.; Xu, J. Nat. Commun. 2020, 11, 3538.
[11]
(f) Zhang, Y.; Chen, Y.; Song, M.; Tan, B.; Jiang, Y.; Yan, C.; Jiang, Y.; Hu, X.; Zhang, C.; Chen, W.; Xu, J. J. Am. Chem. Soc. 2022, 144, 16042.
[11]
(g) Hu, J.; Guo, L.-D.; Chen, W.; Jiang, Y.; Pu, F.; Ning, C.; Xu, J. Org. Lett. 2022, 24, 7416.
[11]
(h) Hu, J.-P.; Xu, J. Chin. Chem. Lett. 2024, 35, 108733.
[12]
Zhong, J.-X.; Chen, K.-W.; Qiu, Y.-Y.; He, H.-B.; Gao, S. Org. Lett. 2019, 21, 3741.
[13]
(a) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Am. Chem. Soc. 2019, 141, 8431.
[13]
(b) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Org. Chem. 2019, 84, 14069.
[13]
(c) Wright, B. A.; Regni, A.; Chaisan, N.; Sarpong, R. J. Am. Chem. Soc. 2024, 146, 1813.
[13]
(d) Wright, B. A.; Okada, T.; Regni, A.; Luchini, G.; Sowndarya, S. S. V; Chaisan, N.; Kölbl, S.; Kim, S. F.; Paton, R. S.; Sarpong, R. J. Am. Chem. Soc. 2024, 146, 33130.
[14]
Xu, G.; Wu, J.; Li, L.; Lu, Y.; Li, C. J. Am. Chem. Soc. 2020, 142, 15240.
[15]
(a) Cao, M.-Y.; Ma, B.-J.; Gu, Q.-X.; Fu, B.; Lu, H.-H. J. Am. Chem. Soc. 2022, 144, 5750.
[15]
(b) Cao, M.-Y.; Gu, Q.-X.; Long, J.; Fang, X.; Lu, H.-H. Adv. Synth. Catal. 2024, 366, 4194.
[16]
Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem., Int. Ed. 2016, 55, 2577.
[17]
(a) Li, L.-X.; Min, L.; Yao, T.-B.; Ji, S.-X.; Qiao, C.; Tian, P.-L.; Sun, J.-W.; Li, C.-C. J. Am. Chem. Soc. 2022, 144, 18823.
[17]
(b) Zou, Y.-P.; Lai, Z.-L.; Zhang, M.-W.; Peng, J.; Ning, S.; Li, C.-C. J. Am. Chem. Soc. 2023, 145, 10998.
[18]
Wu, B.-L.; Yao, J.-N.; Long, X.-X.; Tan, Z.-Q.; Liang, X.; Feng, L.; Wei, K.; Yang, Y.-R. J. Am. Chem. Soc. 2024, 146, 1262.
[19]
(a) Morita, H.; Takatsu, H.; Shen, Y.-C.; Kobayashi, J. Tetrahedron Lett. 2004, 45, 901.
[20]
Hanessian, S.; Dorich, S.; Menz, H. Org. Lett., 2013, 15, 4134.
[21]
(a) Qiu, Y.-Y.; Zhong, J.-X.; Gao, S. Chem. Comm. 2018, 54, 5554.
[21]
(b) Qiu, Y.-Y. Ph.D. Dissertation, East China Normal University, Shanghai, 2018. (in Chinese)
[21]
(邱远游, 博士论文, 华东师范大学, 上海, 2018.)
[22]
Chen, Y.-Y.; Hu, J.-P.; Guo, L.-D.; Tian, P.-L.; Xu, T.-Y.; Xu, J. Org. Lett. 2019, 21, 4309.
[23]
Chen, Y.-Y.; Guo, L.-D.; Xu, J. Tetrahedron Lett. 2021, 71, 153030.
[24]
Mao, H.-K.; Wang, Q.; Xie, S.; Xu, J. Org. Lett. 2024, 26, 10616.
[25]
(a) Wu, D.-P.; He, Q.; Chen, D.-H.; Ye, J.-L.; Huang, P.-Q. Chin. J. Chem. 2019, 37, 315.
[25]
(b) Huang, P.-Q.; Huang, Y.-H. Chin. J. Chem. 2017, 35, 613.
[25]
(c) Huang, P.-Q.; Huang, Y.-H.; Wang, S.-R. Org. Chem. Front. 2017, 4, 431.
[25]
(d) Huang, P.-Q.; Huang, Y.-H.; Geng, H.; Ye, J.-L. Sci. Rep. 2016, 6, 28801.
[25]
(e) Huang, P.-Q.; Lang, Q.-W.; Wang, A.-E; Zheng, J.-F. Chem. Commun. 2015, 51, 1096.
[25]
(f) Huang, P.-Q.; Huang, Y.-H.; Xiao, K.-J.; Wang, Y.; Xia, X.-E. J. Org. Chem. 2015, 80, 2861.
[25]
(g) Zheng, J.-F.; Qian, X.-Y.; Huang, P.-Q. Org. Chem. Front. 2015, 2, 927.
[26]
(a) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
[26]
(b) Xu, J.; Caro-Diaz, E. J. E.; Theodorakis, E. A. Org. Lett. 2010, 12, 3708.
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