SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 9: 2703 - 2714

DOI: https://doi.org/10.6023/cjoc202204044

综述与进展

自由基多烯环化反应在天然产物全合成中的应用

  • 姚良才 ,
  • 桂敬汉
展开
  • a 上海师范大学化学与材料科学学院 上海 200233
    b 中国科学院上海有机化学研究所 中国科学院天然产物有机合成化学重点实验室 上海 200032

收稿日期: 2022-04-17

  修回日期: 2022-06-02

  网络出版日期: 2022-06-17

基金资助

国家重点研发计划(2021YFF0502400); 国家自然科学基金(22122112); 国家自然科学基金(21871289); 上海市科学技术委员会(21ZR1476400); 上海市扬帆计划(21YF1456400); 国家中医药管理局多学科交叉创新团队(ZYYCXTD-202004)

收起

Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis

  • Liangcai Yao ,
  • Jinghan Gui
Expand
  • a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200233
    b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
* Corresponding author. E-mail:

Received date: 2022-04-17

  Revised date: 2022-06-02

  Online published: 2022-06-17

Supported by

National Key Research and Development Program of China(2021YFF0502400); National Natural Science Foundation of China(22122112); National Natural Science Foundation of China(21871289); Science and Technology Commission of Shanghai Municipality(21ZR1476400); Shanghai Sailing Program(21YF1456400); Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(ZYYCXTD-202004)

Fold

摘要

多环化合物普遍存在于天然产物、合成药物、农药化学品和精细化学品中, 具有广泛的生物活性, 因此如何高效合成多环化合物是有机合成的一个重要研究方向. 近年来, 多烯烃的自由基串联环化反应越来越成为构建多环骨架的一种可靠、简便途径, 然而目前有关自由基串联环化方面的研究论文特别是近年来发展的环氧均裂开环引发自由基多烯环化反应并未被总结归纳. 因此主要综述了自由基多烯环化反应的引发方法及其在多环天然产物合成中的应用, 将着重介绍环氧多烯在Ti(III)作用下的自由基多烯串联环化反应.

关键词： 多环骨架; 环氧多烯; 自由基; 串联环化; 天然产物合成

本文引用格式

姚良才 , 桂敬汉 . 自由基多烯环化反应在天然产物全合成中的应用[J]. 有机化学, 2022 , 42(9) : 2703 -2714 . DOI: 10.6023/cjoc202204044

Abstract

Polycyclic compounds, which exist widely in natural products, synthetic drugs, agrochemicals, fine chemicals, etc. have a wide range of biological activities. Therefore, efficient synthesis of polycyclic compounds is an important research direction in organic synthesis. In recent years, free radical cascade cyclization of polyenes has increasingly become a reliable and concise way to construct polycyclic skeletons. However, the research papers on free radical cascade cyclization, especially those initiated by the homolysis of epoxides, have not been summarized. Therefore, this paper mainly reviews the initiation methods of free radical polyene cascade cyclization and its application in the synthesis of polycyclic natural products, with an emphasis on the Ti(III)-mediated free radical cascade cyclization of polyene epoxides.

Key words： polycyclic skeleton; polyene epoxide; free radical; cascade cyclization; natural product synthesis

参考文献

[1]
Gershenzon, J.; Dudareva, N. Nat. Chem. Biol. 2007, 3, 408.
[2]
de la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2004, 43, 160.
[3]
Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730.
[4]
Wendt, K. U.; Poralla, K.; Schulz, G. E. Science 1997, 277, 1811.
[5]
Jarstfer, M. B.; Blagg, B. S. J.; Rogers, D. H.; Poulter, C. D. J. Am. Chem. Soc. 1996, 118, 13089.
[6]
Stork, G.; Burgstahler, A. W. J..Am. Chem. Soc. 1955, 77, 5068.
[7]
Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890.
[8]
Eschenmoser, A.; Arigoni, D. Helv. Chim. Acta 2005, 88, 3011.
[9]
Ishihara, K.; Nakamura, S.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 4906.
[10]
Surendra, K.; Corey, E. J. J. Am. Chem. Soc. 2012, 134, 11992.
[11]
Surendra, K.; Rajendar, G.; Corey, E. J. J. Am. Chem. Soc. 2014, 136, 642.
[12]
Corey, E. J.; Luo, G.; Lin, S. J. Am. Chem. Soc. 1997, 119, 9927.
[13]
Corey, E. J.; Noe, M. C.; Lin, S. Tetrahedron Lett. 1995, 36, 8741.
[14]
Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324.
[15]
Corey, E. J.; Lin, S.; J. Am. Chem. Soc. 1996, 118, 8765.
[16]
Breslow, R.; Barrett, E.; Mohaosi, E. Tetrahedron Lett. 1962, 3,1207.
[17]
Corey, E. J.; Russey, W. E.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1966, 88, 4750.
[18]
van Tamelen, E. E.; Willett, J. D.; Clayton, R. B.; Lord, K. E. J. Am. Chem. Soc. 1966, 88, 4752.
[19]
Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137.
[20]
Heiba, E. I.; Dessau, R. M.; Koehl, W. J., Jr. J. Am. Chem. Soc. 1968, 90, 5905.
[21]
Bush, J. B., Jr.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903.
[22]
Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659.
[23]
Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759.
[24]
Kates, S. A.; Dombroski, M. A.; Snider, B. B. J. Org. Chem. 1990, 55, 2427.
[25]
Trotta, A. H. J. Org. Chem. 2017, 82, 13500.
[26]
Takada, K.; Kajiwara, H.; Imamura, N. J. Nat. Prod. 2010, 73, 698.
[27]
Baunach, M.; Ding, L.; Bruhn, T.; Bringmann, G.; Hertweck, C. Angew. Chem., Int. Ed. 2013, 52, 9040.
[28]
Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579.
[29]
Kupchan, S. M.; Court, W. A.; Dailey, R. G., Jr.; Gilmore, C. J.; Bryan, R. F. J. Am. Chem. Soc. 1972, 94, 7194.
[30]
Neumann, W. P. Synthesis 1987, 665.
[31]
Houk, K. N.; Paddon-Row, M. N.; Spellmeyer, D. C.; Rondan, N. G.; Nagase, S. J. Org. Chem. 1986, 51, 2874.
[32]
Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
[33]
Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron Lett. 1985, 26, 373.
[34]
Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
[35]
RajanBabu, T. V. J. Am. Chem. Soc. 1987, 109, 609.
[36]
RajanBabu, T. V. J. Org. Chem. 1988, 53, 4522.
[37]
RajanBabu, T. V.; Fukanaga, T. J. Am. Chem. Soc. 1989, 111, 296.
[38]
RajanBabu, T. V.; Fukanaga, T.; Reddy, G. S. J. Am. Chem. Soc. 1989, 111, 1759.
[39]
Curran, D. P.; Rakiewicz, D. M. Tetrahedron 1985, 41, 3943.
[40]
Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448.
[41]
Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
[42]
Green, M. L. H.; Lucas, C. R. J. Chem. Soc., Dalton Trans. 1972, 1000.
[43]
Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849.
[44]
Gansäuer, A.; Pierobon, M.; Bluhm, H. Synthesis 2001, 2500.
[45]
Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561.
[46]
Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101.
[47]
Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849.
[48]
Friedrich, J.; Dolg, M.; Gansäuer, A.; Geich-Gimbel, D.; Lauterbach, T. J. Am. Chem. Soc. 2005, 127, 7071.
[49]
Gansäuer, A.; Pierobon, M. Synlett 2000, 1357.
[50]
Fernández-Mateos, A.; Burón, M. L.; Clemente, R. R.; Silvo, R. A. I.; González, R. R. Synlett 2004, 1011.
[51]
Fernández-Mateos, A.; Teijón, P. H.; Clemente, R. R.; González, R. R.; González, F. S. Synlett 2007, 2718.
[52]
Kondracki, M.-L.; Guyot, M. Tetrahedron 1989, 45, 1995.
[53]
Haruo, Y.; Hasegawa, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1935.
[54]
Rosales, A.; Muñoz-Bascón, J.; Morales-Alcázar, M. V.; Castilla- Alcalá, J. A.; Oltra, E. J. RSC Adv. 2012, 2, 12922.
[55]
Somerville, M. J.; Mollo, E.; Cimino, G.; Rungprom, W.; Garson, M. J. J. Nat. Prod. 2006, 69, 1086.
[56]
Capelle, N.; Braekman, J. C.; Daloze, D.; Tursch, B. Bull. Soc. Chim. Belg. 1980, 89, 399.
[57]
Betancur-Galvis, L.; Zuluaga, C.; Arnó, M.; González, M. A.; Zaragozá, R. J. J. Nat. Prod. 2002, 65, 189.
[58]
Ponomarenko, L. P.; Terent'eva, N. A.; Krasokin, V. B.; Kalinovsky, A. I.; Rasskazov, V. A. Nat. Prod. Commun. 2011, 6, 773.
[59]
Justicia, J.; Oller-López, J. L.; Campaña, A. G.; Oltra, J. E.; Cuerva, J. M.; Buñuel, E.; Cárdenas, D. J. J. Am. Chem. Soc. 2005, 127, 14911.
[60]
Quílez del Moral, J. F.; Pérez, Á.; Herrador, M. M.; Barrero, A. F. J. Nat. Prod. 2019, 82, 9.
[61]
Urones, J. G.; Marcos, I. S.; Basabe, P.; Alonso, C. A.; Diez, D.; Garrido, N. M.; Oliva, I. M.; Rodilla, J. S.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron Lett. 1990, 31, 4501.
[62]
Ting, C. P.; Xu, G.; Zeng, X.; Maimone, T. J. J. Am. Chem. Soc. 2016, 138, 14868.
[63]
Stierle, D. B.; Stierle, A. A.; Patacini, B.; McIntyre, K.; Girtsman, T.; Bolstad, E. J. Nat. Prod. 2011, 74, 2273.
[64]
Franchi, L.; Eigenbrod, T.; Muñoz-Planillo, R.; Nuñez, G. Nat. Immunol. 2009, 10, 241.
[65]
Chen, X.; Zhang, D.; Xu, D.; Zhou, H.; Xu, G. Org. Lett. 2020, 22, 6993.
[66]
Zhou, Z.-W.; Yin, S.; Zhang, H.-Y.; Fu, Y.; Yang, S.-P.; Wang, X.-N.; Wu, Y.; Tang, X.-C.; Yue, J.-M. Org. Lett. 2008, 10, 465.
[67]
Han, M.-L.; Zhang, H.; Yang, S.-P.; Yue, J.-M. Org. Lett. 2012, 14, 486.
[68]
Bergamini, C. M.; Gambetti, S.; Dondi, A.; Cervellati, C. Curr. Pharm. Des. 2004, 10, 1611.
Options
文章导航

/

〈 〉