SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

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

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

Reviews

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

  • Liu Yanze ,
  • Chang Junbiao ,
  • Xie Jingxi
Expand
  • 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).

Fold

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

Cite this article

Liu Yanze , Chang Junbiao , Xie Jingxi . Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2040 -2053 . DOI: 10.6023/cjoc201204029

References

[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.
Options
Outlines

/

〈 〉