Chemical Research in Chinese Universities

, Volume 33, Issue 6, pp 890–894 | Cite as

Total synthesis and biological evaluation of Wewakazole

  • Bohua Long
  • Jingzhao Zhang
  • Xueyan Wang
  • Xudong Tang
  • Zhengzhi Wu


The total synthesis of Wewakazole was achieved on a gram scale, unambiguously confirming its structure. Three different substituted oxazoles present in this natural product were prepared efficiently. Biological evaluation indicated that Wewakazole significantly inhibited cancer cell proliferation in a dose-dependent manner.


Wewakazole Total synthesis Biological evaluation 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

40242_2017_7129_MOESM1_ESM.pdf (2.3 mb)
Total Synthesis of Wewakazole


  1. [1]
    Davidson B. S., Chem. Rev., 1993, 93, 1771CrossRefGoogle Scholar
  2. [2]
    Gribble G. W., Mar. Drugs, 2015, 13, 4044CrossRefPubMedPubMedCentralGoogle Scholar
  3. [3]
    Wang B. G., Gloer J. B., Ji N. Y., Zhao J. C., Chem. Rev., 2013, 113, 3632CrossRefPubMedGoogle Scholar
  4. [4]
    Gribble G. W., Heterocycles, 2012, 84, 157CrossRefGoogle Scholar
  5. [5]
    Gribble G. W., Acc. Chem. Res., 1998, 31, 141CrossRefGoogle Scholar
  6. [6]
    Zhao C., Zhu T., Zhu W., Chin. J. Org. Chem., 2013, 33, 1195CrossRefGoogle Scholar
  7. [7]
    Hu G. P., Yuan J., Sun L., She Z. G., Wu J. H., Lan X. J., Zhu X., Lin Y. C., Chen S. P., Mar. Drugs, 2011, 9, 514CrossRefPubMedPubMedCentralGoogle Scholar
  8. [8]
    Blunt J. W., Copp B. R., Hu W. P., Munro M. H. G., Northcote P. T., Prinsep M. R., Nat. Prod. Rep., 2009, 26, 170CrossRefPubMedGoogle Scholar
  9. [9]
    Blunt J. W., Copp B. R., Munro M. H., Northcote P. T., Prinsep M. R., Nat. Prod. Rep., 2010, 27, 165CrossRefPubMedGoogle Scholar
  10. [10]
    Blunt J. W., Copp B. R., Munro M. H., Northcote P. T., Prinsep M. R., Nat. Prod. Rep., 2011, 28, 196CrossRefPubMedGoogle Scholar
  11. [11]
    Nestor Jr. J. J., Curr. Med. Chem., 2009, 16, 4399CrossRefPubMedGoogle Scholar
  12. [12]
    Newman D. J., Gragg G. M., J. Nat. Prod., 2007, 70, 461CrossRefPubMedGoogle Scholar
  13. [13]
    Nogle L. M., Marquez B. L., Gerwick W. H.,Org. Lett., 2003, 5, 3CrossRefPubMedGoogle Scholar
  14. [14]
    Long B., Tang S., Chen L., Qu S., Chen B., Liu J., Maguire A. R., Wang Z., Liu Y., Zhang H., Xu Z., Ye T., Chem. Commun., 2013, 49, 2977CrossRefGoogle Scholar
  15. [15]
    Long B., Zhang J., Tang X., Wu Z., Org. Biomol. Chem., 2016, 14, 9712CrossRefPubMedGoogle Scholar
  16. [16]
    Valdomir G., Padrónb J. I., Padrónc J. M., Martínc V. S., Davyt D., Synthesis, 2014, 46, 2451CrossRefGoogle Scholar
  17. [17]
    Moni L., Banfi L., Basso A., Carcone L., Rasparini M., Riva R., J. Org. Chem., 2015, 80, 3411CrossRefPubMedGoogle Scholar
  18. [18]
    Davies J. R., Kane P. D., Moody C. J., J. Org. Chem., 2005, 70, 7305CrossRefPubMedGoogle Scholar
  19. [19]
    Bertram A., Maulucci N., New O. M., Nora S. M. M., Pattenden G., Org. Biomol. Chem., 2007, 5, 1541CrossRefPubMedGoogle Scholar
  20. [20]
    Ferreira P. M. T., Castanheira E. M. S., Monteiro L. S., Pereira G., Vilaça H., Tetrahedron, 2010, 66, 8672CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2017

Authors and Affiliations

  • Bohua Long
    • 1
    • 2
    • 3
  • Jingzhao Zhang
    • 4
  • Xueyan Wang
    • 4
  • Xudong Tang
    • 4
  • Zhengzhi Wu
    • 1
    • 2
    • 3
  1. 1.The Fourth People’s Hospital of ShenzhenShenzhenP. R. China
  2. 2.Shenzhen Institute of GeriatricsShenzhenP. R. China
  3. 3.The Second People’s Hospital of ShenzhenShenzhenP. R. China
  4. 4.Key Lab for New Drug Research of TCM and Shenzhen Branch, State R&D Centre for Viro-BiotechResearch Institute of Tsinghua University in ShenzhenShenzhenP. R. China

Personalised recommendations