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2012 , Vol. 32 >Issue 11: 2040 - 2053

DOI: https://doi.org/10.6023/cjoc201204029

综述与进展

芳基氧化偶联试剂在天然活性成分联苯并环辛烯类木脂素合成中的应用进展

  • 刘延泽 ,
  • 常俊标 ,
  • 谢晶曦
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  • a 中国医学科学院协和医学院药用植物研究所 北京 100193;
    b 郑州大学化学系 郑州 450000;
    c 中国医学科学院协和医学院药物研究所 北京 100050

收稿日期: 2012-04-26

  修回日期: 2012-06-14

  网络出版日期: 2012-06-21

基金资助

科技部国际科技合作(No. 2007DFB31610)资助项目.

收起

Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans

  • Liu Yanze ,
  • Chang Junbiao ,
  • Xie Jingxi
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  • a Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193;
    b Department of Chemistry, Zhengzhou University, Zhengzhou 450000;
    c Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100050

Received date: 2012-04-26

  Revised date: 2012-06-14

  Online published: 2012-06-21

Supported by

Project supported by the International Cooperation Program of the Ministry of Science and Technology of China (No. 2007DFB31610).

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摘要

联苯并环辛二烯类木脂素是重要的一类天然产物, 具有保肝等多种生物活性. 近20余年来各国学者对其全合成研究进行了卓有成效的探索, 尤其在芳基氧化偶联试剂的应用方面取得了很多进展. 作者结合在该领域多年的工作积累, 对分子内和分子间芳基氧化偶联试剂在联苯并环辛二烯木脂素合成中的应用及全合成研究的进展进行了综述, 以便对同道起到参考与启发作用. 最后提出了新的双片段合成拼接的设想.

关键词： 联苯并环辛二烯; 木脂素; 芳基氧化偶联; 天然产物; 五味子; 全合成

本文引用格式

刘延泽 , 常俊标 , 谢晶曦 . 芳基氧化偶联试剂在天然活性成分联苯并环辛烯类木脂素合成中的应用进展[J]. 有机化学, 2012 , 32(11) : 2040 -2053 . DOI: 10.6023/cjoc201204029

Abstract

Dibenzocyclooctadiene lignans, such as schizandrin, gomisin are a kind of important natural product with significant biological activities, especially for liver disease. Several total synthetic strategies had been investigated and succeed in the application of oxidative coupling reagents including intramolecular and intermolecular coupling such as TlTFA, RuTFA, Fe(ClO4)3, MoCl5, and PhI(OAc)2 etc. These applications of various aryl-aryl oxidative coupling reagents for the synthesis of dibenzocyclooctadiene lignans published in recent 20 years are reviewed, together with author’s experience in this area. Finally, the new synthetic hypothesis through the connection between biphenyl aryl piece and aliphatic piece is proposed.

Key words： dibenzocyclooctadiene; lignans; aryl-aryl oxidative coupling; natural product; Schisandraceae; total synthesis

参考文献

[1] Кочетков, Н.-К.; Хорпцн, А.-Я.; Чижов, О.-С. Ж. Общ. Химин. 1961, 31, 3454.
[2] Xu, L.-J.; Liu, H.-T.; Peng, Y.; Xiao, P.-G. J. Syst. Evol. 2008, 46, 692 (in Chinese).
(许利嘉, 刘海涛, 彭勇, 肖培根, 植物分类学报, 2008, 46, 692.)

[3] Yu, L.-H.; Liu, G.-T. Prog. Chem. 2009, 21, 66 (in Chinese).
(余凌虹, 刘耕陶, 化学进展, 2009, 21, 66.)

[4] Liu, J.-Y.; Wang, Y.-P.; Liu, H.-Z. Spec. Wild Economic Animal Plant Res. 2005, (3), 49 (in Chinese).
(刘继永, 王英平, 刘洪章, 特产研究, 2005, (3), 49.)

[5] Huang, X.-D.; Ren, K. J. Jilin Med. College 2010, 31, 46 (in Chinese).
(黄晓东, 任旷, 吉林医药学院学报, 2010, 31, 46.)

[6] Wei, X.-C. M. S. Thesis, Jilin Agricultural University, Changchun, 2007 (in Chinese).
(魏小川, 硕士论文, 吉林农业大学, 长春, 2007.)

[7] Yang, G.-Y.; Li, Y.-K.; Wang, R.-R.; Li, X.-N.; Xiao, W.-L.; Yang, L.-M.; Pu, J.-X; Zheng, Y.-T.; Sun, H.-D. J. Nat. Prod. 2010, 73, 915.

[8] Panossian, A; Wikman, G. J. Ethnopharmacol. 2008, 118, 183.

[9] Hu, X. CN 1833636, 2006 [Chem. Abstr. 2006, 145, 425852].

[10] Ward, R. S. Tetrahedron 1990, 46, 5029.

[11] Ward, R. S. Nat. Prod. Rep. 1995, 12, 183; 1997, 14, 43.

[12] Carroll, A. R.; Read, R. W. Aust. J. Chem. 1994, 47, 1579.

[13] Whiting, D. A. Nat. Prod. Rep. 1990, 7, 349.

[14] Xie, L.; Chen, L. H.; Xie, J. X. Chin. J. Org. Chem. 1991, 11, 371 (in Chinese).
(谢蓝, 陈立华, 谢晶曦, 有机化学, 1991, 11, 371.)

[15] Chang, J.-B.; Reimer, J.; Xie, J.-X. Chem. Rev. 2005, 105, 4581.

[16] Dahl, R.; Landais, Y.; Lebrun, A.; Lenain, V.; Robin, J.-P. Tetrahedron 1994, 50, 1153.

[17] (a) Tomioka, K.; Ishiguro, T.; Koga, K. Tetrahedron Lett. 1980, 21, 2973.
(b) Tomioka, K.; Ishiguro, T.; Koga, K. Tetrahedron 1984, 10, 1303.

[18] Tomioka, K.; Mizuguchi, H.; Ishiguro, T.; Koga, K. Chem. Pharm. Bull. 1985, 33, 121.

[19] Chang, J.-B.; Xie, J.-X. Acta Pharm. Sin. 1998, 33, 424 (in Chinese).
(常俊标, 谢晶曦, 药学学报, 1998, 33, 424.)

[20] Landais, Y.; Robin, J.-P.; Lebrun, A. Tetrahedron 1991, 47, 3787.

[21] Ward, R.-S.; Hughes, D.-D. Tetrahedron 2001, 57, 2057.

[22] Ward, R.-S.; Hughes, D.-D. Tetrahedron 2001, 57, 4015.

[23] Takeya, T.; Okubo, T.; Nishida, S.; Tobinaga, S. Chem. Pharm. Bull. 1985, 33, 3599.

[24] Tanaka, M.; Ohshima, T.; Mitsuhshi, H.; Maruno, M.; Wakamatsu, T. Tetrahedron 1995, 51, 11693.

[25] Tanaka, M.; Mukaiyama, C.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. J. Org. Chem. 1995, 60, 4339.

[26] Ohshima, T.; Tanaka, M.; Mitsuhshi, H.; Maruno, M.; Wakamatsu, T. Tetrahedron: Asymmetry 1995, 6, 139.

[27] Takeya, T.; Ohguchi, A.; Ara, Y.; Tobinaga, S. Chem. Pharm. Bull. 1994, 42, 430.

[28] Takeya, T.; Ohguchi, A.; Tobinaga, S. Chem. Pharm. Bull. 1994, 42, 438.

[29] Pelter, A.; Ward, R.-S.; Jones, D.-M.; Maddocks, P. Tetrahedron: Asymmetry 1992, 3, 239.

[30] Chen, L.-H.; Xie, L.; Xie, J.-X. Acta Pharm. Sin. 1991, 26, 20 (in Chinese).
(陈立华, 谢蓝, 谢晶曦, 药学学报, 1991, 26, 20.)

[31] Xie, L.; Xie, J.-X. Chin. Chem. Lett. 1998, 9, 631.

[32] Chang, J.-B.; Xie, J.-X. Sci. China, Ser. B 2000, 43, 323.

[33] Chang, J.-B.; Mcphail, A.-T.; Kong, M.; Xie, J.-X. Chin. Chem. Lett. 1996, 7, 691.

[34] Chang, J.-B.; Xie, J.-X. Chin. Chem. Lett. 1996, 7, 801.

[35] Chang, J.-B.; Xie, J.-X. Chin. Chem. Lett. 2001, 12, 667.

[36] Chang, J.-B.; Xie, J.-X.; Chen, R.-F.; Liu, P. Acta Pharm. Sin. 1999, 34, 913 (in Chinese).
(常俊标, 谢晶曦, 陈荣峰, 刘澎, 药学学报, 1999, 34, 913.)

[37] Chen, L.-H.; Xie, L.; Xie, J.-X. Chin. J. Org. Chem. 1991, 11, 503 (in Chinese).
(陈立华, 谢蓝, 谢晶曦, 有机化学, 1991, 11, 503.)

[38] Song, C.-J.; Zhao, P.; Hu, Z.-Q.; Shi, S.; Cui, Y.; Chang, J.-B. Bioorg. Med. Chem. Lett. 2010, 20, 2297.

[39] Coleman, R.-S.; Gurrala, S.-R. Org. Lett. 2005, 7, 1849.

[40] Coleman, R.-S.; Gurrala, S.-R.; Mitra, S.; Raao, A. J. Org. Chem. 2005, 70, 8932.

[41] Kramer, B.; Averhoff, A.; Waldvogel, S.-R. Angew. Chem., Int. Ed. 2002, 41, 2981.

[42] Kramer, B.; Froehlich, R.; Waldvogel, S.-R. Eur. J. Org. Chem. 2003, 18, 3549.

[43] Planchenault, D.; Dhal, R.; Robin, J.-P. Tetrahedron 1995, 51, 1395.

[44] Robin, J.-P.; Landais, Y. J. Org. Chem. 1988, 53, 224.

[45] Ward, R.-S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron 1996, 52, 1303.

[46] Pelter, A.; Ward, R.-S.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1992, 2249.

[47] Ward, R.-S.; Hughes, D.-D. Tetrahedron 2001, 57, 5633.

[48] Waldvogel, S.-R. Synlett 2002, 622.

[49] Kramer, B.; Frohlich, R.; Bergander, K.; Waldvogel, S.-R. Synthesis 2003, 91.

[50] Xie, J.-X.; Zhou, J.; Zhang, C.-Z.; Yang, J.-H. Sci. China, Ser. B 1983, 9, 823.

[51] Li, Y.; Wang, Q.; Dong, L.-H.; Guo, X.-H.; Wang, W.; Xie, J.-X.; Chang, J.-B. Synthesis 2009, 3383.

[52] Warshawsky, A.-M.; Meyers, A.-I. J. Am. Chem. Soc. 1990, 112, 8090.

[53] Meyers, A.-I.; Flisak, J.-R.; Aitken, R.-A. J. Am. Chem. Soc. 1987, 109, 5446.

[54] Sefkow, M. Top. Curr. Chem. 2005, 243, 185.

[55] Chen, W.-W.; Zhao, Q.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2010, 12, 1072.

[56] Monovich, L.-G.; Huérou, Y.-L.; Rönn, M.; Molander, G.-A. J. Am. Chem. Soc. 2000, 122, 52.

[57] Uemura, M.; Daiman, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 19, 1943.

[58] Molander, G.-A. J. Org. Chem. 2003, 68, 9533.

[59] Hopkinson, M.-N.; Gee, A.-D.; Gouverneur, V. Chem.-Eur. J. 2011, 17, 8248.

[60] Kar, A.; Mangu, N.; Kaiser, H.-M.; Beller, M.; Tse, M.-K. Chem. Commun. 2008, 386.

[61] Feldman, K.-S.; Iyer, M.-R.; Liu, Y.-Z. J. Org. Chem. 2003, 68, 7433.

[62] Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563.
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