Chemical Research in Chinese Universities

, Volume 34, Issue 6, pp 867–870 | Cite as

Stereoselective Synthesis of a Common 3-Oxabicyclo[3.2.0]heptan-2-one Core Building Block Toward Illicium Sesquiterpenes via Desymmetrization

  • Wentan Liu
  • Bo WangEmail author


3-Oxabicyclo[3.2.0]heptan-2-one Illicium sesquiterpene Oxidative coupling 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. [1]
    Oh I. C., Denk T., Friis E. M., Plant Syst. Evol., 2003, 240, 175CrossRefGoogle Scholar
  2. [2]
    Urabe D., Inoue M., Tetrahedron, 2009, 65, 6271CrossRefGoogle Scholar
  3. [3]
    Huang J. M., Yokoyama R., Yang C. S., Fukuyama Y., Tetrahedron Lett., 2000, 41, 6111CrossRefGoogle Scholar
  4. [4]
    Huang J. M., Yang C. S., Tanaka M., Fukuyama Y., Tetrahedron, 2001, 57, 4691CrossRefGoogle Scholar
  5. [5]
    Kouno I., Mori K., Kawano N., Sato S., Tetrahedron Lett., 1989, 30, 7451CrossRefGoogle Scholar
  6. [6]
    Kouno I., Mori K., Okamoto S., Sato S., Chem. Pharm. Bull., 1990, 38, 3060CrossRefGoogle Scholar
  7. [7]
    Huang J. M., Yokoyama R., Yang C. S., Fukuyama Y., J. Nat. Prod., 2001, 64, 428CrossRefGoogle Scholar
  8. [8]
    Ma S. G., Li M., Lin M. B., Li L., Liu Y. B., Qu J., Li Y., Wang X. J., Wang R. B., Xu S., Hou Q., Yu S. S., Org. Lett., 2017, 19, 6160CrossRefGoogle Scholar
  9. [9]
    Birman V. B., Danishefsky S. J., J. Am. Chem. Soc., 2002, 124, 2080CrossRefGoogle Scholar
  10. [10]
    Meng Z., Danishefsky S. J., Angew. Chem. Int. Ed., 2005, 44, 1511CrossRefGoogle Scholar
  11. [11]
    Inone M., Sato T., Hirama M., J. Am. Chem. Soc., 2003, 125, 10772CrossRefGoogle Scholar
  12. [12]
    Inone M., Sato T., Hirama M., Angew. Chem. Int. Ed., 2006, 45, 4843CrossRefGoogle Scholar
  13. [13]
    Inoue M., Lee N., Kasuya S., Sato T., Hirama M., Moriyama M., Fukuyama Y., J. Org. Chem., 2007, 72, 3065CrossRefGoogle Scholar
  14. [14]
    Mehta G., Singh S. R., Angew. Chem. Int. Ed., 2006, 45, 953CrossRefGoogle Scholar
  15. [15]
    He W., Huang J., Sun X. F., Frontier A. J., J. Am. Chem. Soc., 2007, 129, 498CrossRefGoogle Scholar
  16. [16]
    He W., Huang J., Sun X. F., Frontier A. J., J. Am. Chem. Soc., 2008, 130, 300CrossRefGoogle Scholar
  17. [17]
    Shi L., Meyer K. M., Greaney M. F., Angew. Chem. Int. Ed., 2010, 49, 9250CrossRefGoogle Scholar
  18. [18]
    Nazef N., Davis R. D., Greaney M. F., Org. Lett., 2012, 14, 3720CrossRefGoogle Scholar
  19. [19]
    Chen J. W., Gao P., Yu F. M., Yang Y., Zhu S. Z., Zhai H. B., Angew. Chem. Int. Ed., 2012, 51, 5897CrossRefGoogle Scholar
  20. [20]
    Cook S. P., Polara A., Danishefsky S. J., J. Am. Chem. Soc., 2006, 128, 16440CrossRefGoogle Scholar
  21. [21]
    Ohtawa M., Krambis M. J., Cerne R., Schkeryantz J. M., Witkin J. M., Shenvi R. A., J. Am. Chem. Soc., 2017, 139, 9637CrossRefGoogle Scholar
  22. [22]
    Ipatieff V. N., Pines H., J. Am. Chem. Soc., 1939, 61, 3374CrossRefGoogle Scholar
  23. [23]
    Török B., Bartók M., J. Catal., 1995, 151, 315CrossRefGoogle Scholar
  24. [24]
    Gao F., Yan X. X., Shakya T., Baettig O. M., Ait-Mohand-Brunet S., Berghuis A. M., Wright G. D., Auclair K., J. Med. Chem., 2006, 49, 5273CrossRefGoogle Scholar
  25. [25]
    Smith A. M. R., Rzepa H. S., White A. J. P., Billen D., Hii K. K., J. Org. Chem., 2010, 75, 3085CrossRefGoogle Scholar
  26. [26]
    Perkin W. H., J. Chem. Soc., 1887, 51, 22Google Scholar
  27. [27]
    Elinson M. I., Fedukovich S. K., Ugrak B. I., Nikishin G. I., Bull. Russ. Acad. Sci. Div. Chem. Sci.(Engl. Trans l.), 1992, 41, 2332Google Scholar
  28. [28]
    Okimoto M., Takahashi Y., Synthesis, 2002, 15, 2215CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.CAS Key Laboratory of High-Performance Synthetic Rubber and Its Composite Materials, Key Laboratory of Green Chemistry and Process of Jilin Province, Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchunP. R. China
  2. 2.University of Chinese Academy of SciencesBeijingP. R. China
  3. 3.University of Science and Technology of ChinaHefeiP. R. China

Personalised recommendations