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Acta Chimica Sinica >

2013 , Vol. 71 >Issue 03: 295 - 298

DOI: https://doi.org/10.6023/A13010018

Article

Interrupted Fisher Indole Synthesis and Its Applications to Alkaloid Synthesis

  • Li Sena ,
  • Han Jing ,
  • Li Ang
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  • a School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016;
    b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2013-01-05

  Online published: 2013-01-25

Supported by

Project supported by the National Basic Research Program (973 Program) of China (No. 2013CB836900), the Natural Science Foundation of China (Nos.21172235, 21222202, and 21290180), Shanghai Pujiang Plan (No. 12PJ1410800) and the Chinese Academy of Sciences.

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Abstract

Fisher indole synthesis is an important method in organic synthesis. Recently, Garg and Liang developed interrupted Fisher indole synthesis and applied it in the synthesis of a series of natural products and natural product-like compounds. Here we highlight their recent progress under this topic.

Key words： Fisher indole synthesis; [3,3]-sigmatropic rearrangement; Cu-catalyzed C—N bond formation; aspidophylline A; total synthesis

Cite this article

Li Sena , Han Jing , Li Ang . Interrupted Fisher Indole Synthesis and Its Applications to Alkaloid Synthesis[J]. Acta Chimica Sinica, 2013 , 71(03) : 295 -298 . DOI: 10.6023/A13010018

References

[1] Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.

[2] Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458.

[3] (a) Song, H.; Yang, J.; Chen, W.; Qin, Y. Org. Lett. 2006, 8, 6011;

     (b) Yang, J.; Wu, H. X.; Shen, L. Q.; Qin, Y. J. Am. Chem. Soc.2007, 129, 13794;

     (c) Shen, L. Q.; Zhang, M.; Wu, Y.; Qin, Y.Angew. Chem., Int. Ed. 2008, 47, 3618;

     (d) Zhang, M.; Huang, X.P.; Shen, L. Q.; Qin, Y. J. Am. Chem. Soc. 2009, 131, 6013.

[4] (a) Jones, S. B.; Simmons, B.; MacMillan, D. W. C. J. Am. Chem.Soc. 2009, 131, 13606;

     (b) Jones, S. B.; Simmons, B.; Mastracchio,A.; MacMillan, D. W. C. Nature 2011, 475, 183.

[5] (a) Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132, 13226;

     (b) Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008;

     (c) Zi,W.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2012, 134, 9126;

     (d) Fan, F.;Xie, W.; Ma, D. Org. Lett. 2012, 14, 1405.

[6] Zhan, F.; Liang, G. Angew. Chem., Int. Ed. 2013, 52, 1266.

[7] (a) Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N.K. Tetrahedron 2010, 66, 4687;

     (b) Çelebi-Ölçüm, N.; Boal, B. W.;Huters, A. D.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2011,133, 5752;

     (c) Schammel, A. W.; Chiou, G.; Garg, N. K. J. Org.Chem. 2012, 77, 725;

     (d) Schammel, A. W.; Chiou, G.; Garg, N. K.Org. Lett. 2012, 13, 4556.

[8] Subramaniam, G.; Hiraku, O.; Hayashi, M.; Koyano, T.; Komiyama,K.; Kam, T. S. J. Nat. Prod. 2007, 70, 1783.

[9] Zu, L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877.

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