Citation: Wu Jinghua, Wang Cheng, Chen Pengquan, Ma Zhiqiang. Synthetic Progress of Natural Products Gracilioethers and Hippolachnin A[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3289-3299. doi: 10.6023/cjoc202003014 shu

Synthetic Progress of Natural Products Gracilioethers and Hippolachnin A

  • Corresponding author: Ma Zhiqiang, cezqma@scut.edu.cn
  • Received Date: 6 March 2020
    Revised Date: 8 April 2020
    Available Online: 17 April 2020

    Fund Project: the National Program on Key Research Project 2016YFA0602900the National Natural Science Foundation of China 21871098the National Natural Science Foundation of China 21672073Project supported by the National Program on Key Research Project (No. 2016YFA0602900), the Science and Technology Program of Guangzhou City (No. 201707010073) and the National Natural Science Foundation of China (Nos. 21672073, 21871098)the Science and Technology Program of Guangzhou City 201707010073

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  • Gracilioethers and hippolachnin A were isolated from marine sponge. Gracilioethers showed antimalarial activity while hippolachnin A exhibited strong antifungal activity. Their fascinating structures and outstanding biological activities have attracted attentions from chemists. Progress on the synthesis of gracilioethers with tricyclic skeleton and hippolachnin A are reviewed in terms of the key strategies employed.
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    1. [1]

      Cragg, G. M.; Newman, D. J. Biochim. Biophys. Acta, Gen. Subj. 2013, 1830, 3670.  doi: 10.1016/j.bbagen.2013.02.008

    2. [2]

      Ueoka, R.; Nakao, Y.; Kawatsu, S.; Yaegashi, J.; Matsumoto, Y.; Matsunaga, S.; Furihata, K.; Soest, R. W. M. V.; Fusetani, N. J. Org. Chem. 2009, 74, 4203.  doi: 10.1021/jo900380f

    3. [3]

      Festa, C.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Monti, M. C.; Casapullo, A.; D'Amore, C.; Renga, B.; Mencarelli, A.; Petek, S.; Bifulco, G.; Fiorucci, S.; Zampella, A. J. Med. Chem. 2012, 55, 8303.  doi: 10.1021/jm300911g

    4. [4]

      (a) Festa, S.; De Marino, S.; D'Auria, M. V.; Deharo, E.; Gonzalez, G.; Deyssard, C.; Petek, S.; Bifulco, G.; Zampella, A. Tetrahedron 2012, 68, 10157.
      (b) Festa, C.; D'Amore, C.; Renga, B.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Bifulco, G.; Zampella, A.; Fiorucci, S. Mar. Drugs 2013, 11, 2314.

    5. [5]

      Piao, S.; Song, Y.; Jiao, W.; Yang, F.; Liu, X.; Chen, W.; Han, B.; Lin, H. Org. Lett. 2013, 15, 3526.  doi: 10.1021/ol400933x

    6. [6]

      (a) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449.
      (b) Poplata, S.; Tröster, A.; Zou, Y.-Q.; Bach, T. Chem. Rev. 2016, 116, 9748.
      (c) Salomon, R. G. Tetrahedron 1983, 39, 485.

    7. [7]

      Rasik, C. M.; Brown, M. K. Angew. Chem., Int. Ed. 2014, 53, 14522.  doi: 10.1002/anie.201408055

    8. [8]

      Ruider, S. A.; Sandmeier, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 2378.  doi: 10.1002/anie.201410419

    9. [9]

      Ruider, S. A.; Carreira, E. M. Org. Lett. 2016, 18, 220.  doi: 10.1021/acs.orglett.5b03356

    10. [10]

      McCallum, M. E.; Rasik, C. M.; Wood, J. L.; Brown, M. K. J. Am. Chem. Soc. 2016, 138, 2437.  doi: 10.1021/jacs.5b13586

    11. [11]

      Xu, Z. J.; Wu, Y. Chem.-Eur. J. 2017, 23, 2026.  doi: 10.1002/chem.201605776

    12. [12]

      Li, Q.; Zhao, K.; Peuronen, A.; Rissanen, K.; Enders, D.; Tang, Y. J. Am. Chem. Soc. 2018, 140, 1937.  doi: 10.1021/jacs.7b12903

    13. [13]

      Shen, X.; Peng, X.; Wong, H. N. C. Org. Lett. 2016, 18, 1032.  doi: 10.1021/acs.orglett.6b00161

    14. [14]

      Winter, N.; Trauner, D. J. Am. Chem. Soc. 2017, 139, 11706.  doi: 10.1021/jacs.7b06815

    15. [15]

      Datta, R.; Ghosh, S. J. Org. Chem. 2017, 82, 7675.  doi: 10.1021/acs.joc.7b01179

    16. [16]

      (a) Rasik, C. M.; Brown M. K. J. Am. Chem. Soc. 2013, 135, 1673.
      (b) Rasik, C. M.; Brown, M. K. Synlett 2014, 760.
      (c) Wang, Y.; Wei, D.; Li, Z.; Zhu, Y.; Tang, M. J. Phys. Chem. A 2014, 118, 4288.
      (d) Rasik, C. M.; Hong, Y. J.; Tantillo, D. J.; Brown, M. K. Org. Lett. 2014, 16, 5168.
      (e) Huston, R.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 1563.
      (f) Nelson, S. G.; Dura, R. D.; Peelen, T. J. Org. React. 2012, 82, 471.
      (g) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.

    17. [17]

      (a) Godula, K. Science 2006, 312, 67.
      (b) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
      (c) Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362.

    18. [18]

      (a) Chen, M. S.; White, M. C. Science 2007, 318, 783.
      (b) Bigi, M. A.; Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2012, 134, 9721.
      (c) Shi, G.; Zhang, Y. Adv. Synth. Catal. 2014, 356, 1419.

    19. [19]

      (a) Song, L.; Yao, H.; Zhu, L.; Tong, R. Org. Lett. 2013, 15, 6.
      (b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.

    20. [20]

      (a) Dias, E. L.; Brookhart, M.; White, P. S. Chem. Commun. 2001, 423.
      (b) Gao, H.; Zhang, J. Chem.-Eur. J. 2012, 18, 2777.

    21. [21]

      (a) Smith, C. D. J. Am. Chem. Soc. 1966, 88, 4273.
      (b) Tabushi, I.; Yamamura, K.; Yoshida, Z. J. Am. Chem. Soc. 1972, 94, 787.
      (c) Petrov, V. A.; Vasil'ev, N. V. Curr. Org. Synth. 2006, 3, 215.

    22. [22]

      (a) Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176.
      (b) Ammann, S. E.; Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2014, 136, 10834.
      (c) Malik, M.; Witkowski, G.; Jaroz, S. Org. Lett. 2014, 16, 3816.
      (d) White, M. C. J. Am. Chem. Soc. 2013, 135, 14052.

    23. [23]

      Morrill, L. A.; Susick, R. B.; Chari, J. V.; Garg, N. K. J. Am. Chem. Soc. 2019, 141, 12423.  doi: 10.1021/jacs.9b05588

    24. [24]

      Kiyama, M.; Isoda, Y.; Nishimoto, M.; Kobayashi, A.; Togawa, D.; Hirao, N.; Kuboki, A.; Ohira, S.; Tetrahedron Lett. 2005, 46, 7483.  doi: 10.1016/j.tetlet.2005.09.011

    25. [25]

      Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 2005, 3942.  doi: 10.1002/ejoc.200500296

    26. [26]

      (a) Blay, G.; Garcia, B.; Molina, E.; Pedro, J. R. Org. Lett. 2005, 7, 3291.
      (b) Paquette, L. A.; Green, K. E.; Gleiter, R.; Schäfer, W.; Gallucci, J. C. J. Am. Chem. Soc. 1984, 106, 8232.

    27. [27]

      Dauben, W. G.; Koch, K.; Smith, S. L.; Chapman, O. L. J. Am. Chem. Soc. 1963, 85, 2616.  doi: 10.1021/ja00900a021

    28. [28]

      Reetz, M. T.; Chatziiosifidis, I.; Schwellnus, K. Angew. Chem. 1981, 93, 716.  doi: 10.1002/ange.19810930837

    29. [29]

      (a) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
      (b) RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408.
      (c) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525.
      (d) Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561.

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