综述与进展

虎皮楠生物碱全合成研究进展

  • 毛海康 ,
  • 徐晶
展开
  • a 哈尔滨工业大学化工与化学学院 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: 2024-09-16

  修回日期: 2024-10-31

  网络出版日期: 2024-12-19

基金资助

国家自然科学基金(22271136); 国家自然科学基金(22471117); 深圳市科技创新委员会(JCYJ20220814203252001); 深圳市小分子药物发现与合成重点实验室(ZDSYS20190902093215877); 广东省催化化学重点实验室(2020B121201002); 广东省创新团队(2019BT02Y335); 广东省教育厅高校基础研究重大项目(2021ZDZX2035); 广东省普通高校创新团队(2020KCXTD016)

Recent Progress in the Total Synthesis of Daphniphyllum Alkaloids

  • Haikang Mao ,
  • Jing Xu
Expand
  • 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

Received date: 2024-09-16

  Revised date: 2024-10-31

  Online published: 2024-12-19

Supported by

National Natural Science Foundation of China(22271136); National Natural Science Foundation of China(22471117); Shenzhen Science, Technology and Innovation Commission(JCYJ20220814203252001); Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis(ZDSYS20190902093215877); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Guangdong Innovative Program(2019BT02Y335); Education Department of Guangdong Province, Key Research Projects in Colleges and Universities in Guangdong Province(2021ZDZX2035); Innovative Team of Universities in Guangdong Province(2020KCXTD016)

摘要

自1909年学界首次分离虎皮楠生物碱以来, 至今已有超过300个虎皮楠生物碱被分离报道. 这些虎皮楠生物碱因其广泛的生物活性以及复杂多变的多环骨架结构, 吸引了众多有机合成化学家的关注. 目前为止, 已有40多个虎皮楠生物碱的全合成得以完成. 选取了自2021年起全球不同课题组对27个虎皮楠生物碱的全合成的研究工作, 并对其进行了归纳和总结.

本文引用格式

毛海康 , 徐晶 . 虎皮楠生物碱全合成研究进展[J]. 有机化学, 2025 , 45(3) : 866 -880 . DOI: 10.6023/cjoc202409017

Abstract

Since the isolation of the first member in 1909, over 300 Daphniphyllum alkaloids have been isolated to date. These Daphniphyllum alkaloids have attracted the attention of many organic chemists due to their wide range of biological activities and complex, diverse and polycyclic skeletal structures. So far, more than 40 Daphniphyllum alkaloids have been synthesized. In this review, the research works of different research groups on the total synthesis of 27 Daphniphyllum alkaloids since 2021 are summarized.

参考文献

[1]
Zhen, M.; Min, T.-L. Chinese Flora (Zhongguo Zhiwu Zhi), Vol. 45(1), Science Press, Beijing, 1980, p. 1. (in Chinese)
[1]
(郑勉, 闵天禄, 中国植物志, 第45(1)卷, 科学出版社, 北京, 1980, p. 1.)
[2]
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.)
[3]
Yagi, S. Kyoto Igaku Zasshi 1909, 6, 208.
[4]
(a) Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936.
[4]
(b) Dong, M.; Zhang, M.-L.; Shi, Q.-W.; Gu, Y.-C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646.
[4]
(c) Yang, S.-P.; Yue, J.-M. Acta Pharmacol. Sin. 2012, 33, 1147.
[4]
(d) Wu, H.; Zhang, X.; Ding, L.; Chen, S.; Yang, J.; Xu, X. Planta Med. 2013, 79, 1589.
[4]
(e) Liang, X.; Yang, X.-Z.; Chen, L.; Jiang, S.; Chen, Y.-D.; Deng, Q.-Y.; Chen, X.-G.; Yuan, J.-Q. Med. Chem. Res. 2021, 30, 1.
[5]
(a) Heathcock, C. H.; Davidsen, S. K.; Mills, S.; Sanner, M. A. J. Am. Chem. Soc. 1986, 108, 5650.
[5]
(b) Ruggeri, R. B.; Heathcock, C. H. J. Org. Chem. 1990, 55, 3714.
[5]
(c) Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120.
[5]
(d) Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734.
[5]
(e) Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532.
[5]
(f) Stafford, J. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5433.
[5]
(g) Ruggeri, R. B.; McClure, K. F.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 1530.
[5]
(h) Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575.
[6]
Weiss, M. E.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 11501.
[7]
(a) Lu, Z.; Li, Y.; Deng, J.; Li, A. Nat. Chem. 2013, 5, 679.
[7]
(b) Li, J.; Zhang, W.; Zhang, F.; Chen, Y.; Li, A. J. Am. Chem. Soc. 2017, 139, 14893.
[7]
(c) Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A. Angew. Chem., Int. Ed. 2018, 57, 952.
[7]
(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.
[8]
(a) Shvartsbart, A.; Smith, A. B., III. J. Am. Chem. Soc. 2014, 136, 870.
[8]
(b) Shvartsbart, A.; Smith, A. B., III. J. Am. Chem. Soc. 2015, 137, 3510.
[9]
Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem., Int. Ed. 2016, 55, 2577.
[10]
Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2016, 55, 6067.
[11]
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.
[12]
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.
[13]
(a) Guo, L.-D.; Chen, Y.; Xu, J. Acc. Chem. Res. 2020, 53, 2726.
[13]
(b) Chen, Y.; Hu, J.; Guo, L.-D.; Zhong, W.; Ning, C.; Xu, J. Angew. Chem., Int. Ed. 2019, 58, 7390.
[13]
(c) Guo, L.-D.; Hou, J.; Tu, W.; Zhang, Y.; Zhang, Y.; Chen, L.; Xu, J. J. Am. Chem. Soc. 2019, 141, 11713.
[13]
(d) Guo, L.-D.; Hu, J.; Zhang, Y.; Tu, W.; Zhang, Y.; Pu, F.; Xu, J. J. Am. Chem. Soc. 2019, 141, 13043.
[13]
(e) Guo, L.-D.; Zhang, Y.; Hu, J.; Ning, C.; Fu, H.; Chen, Y.; Xu, J. Nat. Commun. 2020, 11, 3538.
[14]
Xu, B.; Wang, B.; Xun, W.; Qiu, F. G. Angew. Chem., Int. Ed. 2019, 58, 5754.
[15]
Zhong, J.; Chen, K.; Qiu, Y.; He, H.; Gao, S. Org. Lett. 2019, 21, 3741.
[16]
(a) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Am. Chem. Soc. 2019, 141, 8431.
[16]
(b) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Org. Chem. 2019, 84, 14069.
[17]
Xu, G.; Wu, J.; Li, L.; Lu, Y.; Li, C. J. Am. Chem. Soc. 2020, 142, 15240.
[18]
(a) Chattopadhyay, A. K.; Hanessian, S. Chem. Rev. 2017, 117, 4104.
[18]
(b) Zhong, J.; Wang, H.; Zhang, Q.; Gao, S. In The Alkaloids, Ed.: Knölker, H.-J., Academic Press, New York, 2021, Vol. 85, pp. 113-176.
[18]
(c) Gierok, J.; Hiersemann, M. Eur. J. Org. Chem. 2024, 27, e202400370.
[19]
Wang, B.; Xu, B.; Xun, W.; Guo, Y.; Zhang, J.; Qiu, F. G. Angew. Chem., Int. Ed. 2021, 60, 9439.
[20]
Cao, M.-Y.; Ma, B.-J.; Gu, Q.-X.; Fu, B.; Lu, H.-H. J. Am. Chem. Soc. 2022, 144, 5750.
[21]
Zi, W.; Zuo, Z.; Ma, D. Acc. Chem. Res. 2015, 48, 702.
[22]
Cao, M.-Y.; Gu, Q.-X.; Long, J.; Fang, X.; Lu, H.-H. Adv. Synth. Catal. 2024, 366, 4194.
[23]
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.
[24]
Min, L.; Liu, X.; Li, C.-C. Acc. Chem. Res. 2020, 53, 703.
[25]
RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525.
[25]
(b) Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964.
[26]
Zou, Y.-P.; Lai, Z.-L.; Zhang, M.-W.; Peng, J.; Ning, S.; Li, C.-C. J. Am. Chem. Soc. 2023, 145, 10998.
[27]
Diaba, F.; Martínez-Laporta, A.; Bonjoch, J. J. Org. Chem. 2014, 79, 9365.
[28]
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.
[29]
Xing, X.; Xu, C.; Chen, B.; Li, C.; Virgil, S. C.; Grubbs, R. H. J. Am. Chem. Soc. 2018, 140, 17782.
[30]
(a) Hutchins, R. O.; Kacher, M.; Rua, L. J. Org. Chem. 1975, 40, 923.
[30]
(b) Kabalka, G. W.; Yang, D. T. C.; Baker, J. D. J. Org. Chem. 1976, 41, 574.
[31]
Lee, K. S.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253.
[32]
(a) Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682.
[32]
(b) Shibuya, M.; Tomizawa, M.; Iwabuchi, Y. J. Org. Chem. 2008, 73, 4750.
[33]
(a) Xie, S.; Chen, Y.; Zhang, Y.; Zhang, Z.; Hu, X.; Yan, C.; Xu, J. Cell. Rep. Phys. Sci. 2024, 5, 101855.
[33]
(b) Chen, Y.; Chen, W.; Zhang, Z.; Xu, J. Chin. J. Chem. 2024, 42, 1267.
[34]
Hu, J.; Guo, L.-D.; Chen, W.; Jiang, Y.; Pu, F.; Ning, C.; Xu, J. Org. Lett. 2022, 24, 7416.
[35]
Ando, M.; Ohhara, H.; Takase, K. Chem. Lett. 1986, 15, 879.
[36]
von Braun, J. Ber. Dtsch. Chem. Ges. 1904, 37, 3210.
[37]
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.
[38]
Su, S.; Lin, C.; Zhai, H. Angew. Chem., Int. Ed. 2023, 62, e202303402.
[39]
Justicia, J.; Álvarez de Cienfuegos, L.; Campaña, A. G.; Miguel, D.; Jakoby, V.; Gansäuer, A.; Cuerva, J. M. Chem. Soc. Rev. 2011, 40, 3525.
[40]
Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2008, 130, 13778.
[41]
Crossley, S. W. M.; Tong, G.; Lambrecht, M. J.; Burdge, H. E.; Shenvi, R. A. J. Am. Chem. Soc. 2020, 142, 11376.
[42]
Zhang, W.; Lu, M.; Ren, L.; Zhang, X.; Liu, S.; Ba, M.; Yang, P.; Li, A. J. Am. Chem. Soc. 2023, 145, 26569.
[43]
Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 1990, 533.
[44]
Grierson, D. Org. React. 1990, 39, 85.
[45]
(a) Trost, B. M. Angew. Chem., Int. Ed. 1986, 25, 1.
[45]
(b) Trost, B. M.; Zhang, L.; Lam, T. M. Org. Lett. 2018, 20, 3938.
[46]
Jones, G.; Stanforth, S. P. Org. React. 2000, 56, 355.
[47]
Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.
[48]
Yang, S.-P.; Yue, J.-M. Org. Lett. 2004, 6, 1401.
[49]
Crout, D. H. G.; Rathbone, D. L. J. Chem. Soc., Chem. Commun. 1987, 1987, 290.
[50]
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.
[51]
(a) Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065.
[51]
(b) Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
[51]
(c) Schafroth, M. A.; Zuccarello, G.; Krautwald, S.; Sarlah, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2014, 53, 13898.
[51]
(d) Sandmeier, T.; Krautwald, S.; Zipfel, H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363.
[51]
(e) Rössler, S. L.; Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139, 3603.
[51]
(f) Sandmeier, T.; Goetzke, F. W.; Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2019, 141, 12212.
[51]
(g) Rössler, S. L.; Petrone, D. A.; Carreira, E. M. Acc. Chem. Res. 2019, 52, 2657.
[52]
Alektiar, S. N.; Han, J.; Dang, Y.; Rubel, C. Z.; Wickens, Z. K. J. Am. Chem. Soc. 2023, 145, 10991.
[53]
Evans, R. W.; Zbieg, J. R.; Zhu, S.; Li, W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 16074.
[54]
Jang, H.-Y.; Hughes, F. W.; Gong, H.; Zhang, J.; Brodbelt, J. S.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 6174.
[55]
Kuwano, R.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 1017.
[56]
Wright, B. A.; Regni, A.; Chaisan, N.; Sarpong, R. J. Am. Chem. Soc. 2024, 146, 1813.
[57]
Comins, D. L.; Brooks, C. A.; Ingalls, C. L. J. Org. Chem. 2001, 66, 2181.
[58]
Toma, T.; Shimokawa, J.; Fukuyama, T. Org. Lett. 2007, 9, 3195.
[59]
Huisgen, R.; Juppe, G. Chem. Ber. 1961, 94, 2332.
[60]
(a) Wright, S. W.; Choi, C.; Chung, S.; Boscoe, B. P.; Drozda, S. E.; Mousseau, J. J.; Trzupek, J. D. Org. Lett. 2015, 17, 5204.
[60]
(b) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 1995, 317.
[60]
(c) Leibler, I. N. M.; Tekle-Smith, M. A.; Doyle, A. G. Nat. Commun. 2021, 12, 6950.
[61]
Nagata, W.; Yoshioka, M.; Hirai, S. Tetrahedron Lett. 1962, 3, 461.
[62]
Brown, C. A.; Yamaichi, A. J. Chem. Soc.,Chem. Commun. 1979, 3, 100.
[63]
Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
[64]
Padwa, A.; Jacquez, M. N.; Schmidt, A. J. Org. Chem. 2004, 69, 33.
[65]
Winter, N.; Trauner, D. J. Am. Chem. Soc. 2017, 139, 11706.
文章导航

/