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Synthesis and Transformations of Naphtho[2,3-B]Furans (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

A systematic summary is presented for methods for the synthesis of naphtho[2,3-b]furans developed over the past twenty years. Natural occurrence of these compounds as well as their biological activity and transformations are reviewed.

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References

  1. J. Correa and J. Romo, Tetrahedron, 22, 685 (1966).

    Article  CAS  Google Scholar 

  2. K. Hayashi, H. Nakamura, and H. Mitsuhashi, Phytochemistry, 12, 2931 (1973).

    Article  CAS  Google Scholar 

  3. K. Naya, Y. Miyoshi, H. Mori, K. Takai, and M. Nakanishi, Chem. Lett., 5, 73 (1976).

    Article  Google Scholar 

  4. E. Okuyama, K. Umeyama, S. Ohmori, M. Yamazaki, and M. Satake, Chem. Pharm. Bull., 42, 2183 (1994).

    Article  CAS  Google Scholar 

  5. S. Abdo, M. Bernardi, G. Marinoni, G. Mellerio, S. Samaniego, G. Vidari, and P. V. Finzi, Phytochemistry, 31, 3937 (1992).

    Article  CAS  Google Scholar 

  6. J. Jakupovic, V. P. Pathak, M. Grenz, S. Banerjee, C. Wolfrum, R. N. Baruah, and F. Bohlmann, Phytochemistry, 26, 1049 (1987).

    Article  CAS  Google Scholar 

  7. F. Bohlmann and M. Bapuji, Phytochemistry, 21, 681 (1982).

    Article  CAS  Google Scholar 

  8. F. Bohlmann and C. Zdero, Chem. Ber., 111, 3140 (1978).

    Article  CAS  Google Scholar 

  9. F. Bohlmann, J. Ziesche, R. M. King, and H. Robinson, Phytochemistry, 19, 2675 (1980).

    Article  CAS  Google Scholar 

  10. F. Bohlmann and C. Zdero, Phytochemistry, 21, 2537 (1982).

    Article  CAS  Google Scholar 

  11. F. Bohlmann, C. Zdero, J. Jakupovic, L. Misra, S. Bannerjee, P. Singh, R. N. Baruah, M. A. Metwally, G. Schmeda-Hirschmann, L. P. H. Vincent, R. M. King, and H. Robinson, Phytochemistry, 24, 1249 (1985).

    Article  CAS  Google Scholar 

  12. P. Torres, R. Chinchilla, M. C. Asensi, and M. Grande, Phytochemistry, 28, 3093 (1989).

    Article  CAS  Google Scholar 

  13. M. Doe, Y. Hirai, T. Kinoshita, K. Shibata, H. Haraguchi, and Y. Morimoto, Chem. Lett., 33, 714 (2004).

    Article  CAS  Google Scholar 

  14. M. Doe, T. Shibue, H. Haraguchi, and Y. Morimoto, Org. Lett., 7, 1765 (2005).

    Article  CAS  Google Scholar 

  15. Q. Liu, L. Shen, T.-T. Wang, C.-J. Chen, W.-Y. Qi, and K. Gao, Food Chem., 122, 55 (2010).

    Article  CAS  Google Scholar 

  16. C. Ito, S. Katsuno, Y. Kondo, H. T.-W. Tan, and H. Furakawa, Chem. Pharm. Bull., 48, 339 (2004).

    Article  Google Scholar 

  17. M. Ogawa, J. Koyanagi, T. Sugaya, T. Tsuda, H. Ohguchi, K. Nakayama, K. Yamamoto, and A. Tanaka, Biosci., Biotechnol., Biochem., 70, 1009 (2006).

    Article  CAS  Google Scholar 

  18. A. Reichstein, S. Vortherms, S. Bannwitz, J. Tentrop, K. Prinz, and K. Mueller, J. Med. Chem., 55, 7273 (2012).

    Article  CAS  Google Scholar 

  19. R. Cavier, J.-P. Buisson, J. Lemoine, and R. Royer, Eur. J. Med. Chem., 73 (1981).

  20. R. Cavier, J.-P. Buisson, and R. Royer, Eur. J. Med. Chem., 91 (1982).

  21. R. Cavier, P. Demerseman, J. Einhorn, and R. Royer, Eur. J. Med. Chem., 175 (1983).

  22. C. Bilger, P. Demerseman, J.-P. Buisson, R. Royer, P. Gayral, and J. Fourniat, Eur. J. Med. Chem., 213 (1987).

  23. L. Garuti, A. Ferranti, G. Giovanninetti, and R. Gaggi, Farmaco, Ed. Sci., 38, 527 (1983).

    CAS  Google Scholar 

  24. J. Wrobel, J. Sredy, C. Moxham, A. Dietrich, Z. Li, D. R. Sawicki, L. Seestaller, L. Wu, A. Katz, D. Sullivan, C. Tio, and Z.-Y. Zhang, J. Med. Chem., 42, 3199 (1999).

    Article  CAS  Google Scholar 

  25. J.-Z. Liu, S.-E. Zhang, F. Nie, Y. Yang, Y.-B. Tang, W. Yin, J.-Y. Tian, F. Ye, and Z. Xiao, Bioorg. Med. Chem. Lett., 23, 6217 (2013).

    Article  CAS  Google Scholar 

  26. Z. Jiang, H. Wang, H. Hu, J. Xu, Y. Hu, X. Li, Y. Ye, J. Wang, and Q. Li, WO Pat. Appl. 2012119265.

  27. Z. Jiang, Y. Hu, J. Wang, Y. Ye, X. Li, H. Xu, H. Yang, and Y. Fu, WO Pat. Appl. 2013166618.

  28. H. M. Meshram, K. C. Sekhar, Y. S. S. Ganesh, and J. S. Yadav, Synlett, 1273 (2000).

  29. Z. Wang, J. Gu, H. Jing, and Y. Liang, Synth. Commun., 39, 4079 (2009).

    Article  CAS  Google Scholar 

  30. Y. Hirai, M. Doe, T. Kinoshita, and Y. Morimoto, Chem. Lett., 33, 136 (2004).

    Article  CAS  Google Scholar 

  31. K. C. Mascall and P. A. Jacobi, Tetrahedron Lett., 53, 1620 (2012).

    Article  CAS  Google Scholar 

  32. M. P. Kumar and R.-S. Liu, J. Org. Chem., 71, 4951 (2006).

    Article  CAS  Google Scholar 

  33. A. S. Droz, U. Neidlein, S. Anderson, P. Seiler, and F. Diederich, Helv. Chim. Acta, 84, 2243 (2001).

    Article  CAS  Google Scholar 

  34. X. Zhang, S. Sarkar, and R. C. Larock, J. Org. Chem., 71, 236 (2006).

    Article  CAS  Google Scholar 

  35. K. Niimi, H. Mori, E. Miyazaki, I. Osaka, H. Kakizoe, K. Takimiya, and C. Adachi, Chem. Commun., 48, 5892 (2012).

    Article  CAS  Google Scholar 

  36. M. Nakano, H. Mori, S. Shinamura, and K. Takimiya, Chem. Mater., 24, 190 (2012).

    Article  CAS  Google Scholar 

  37. T. Konno, J. Chae, T. Ishihara, and H. Yamanaka, Tetrahedron, 60, 11695 (2004).

    Article  CAS  Google Scholar 

  38. J. Svoboda, M. Nic, and J. Palecek, Collect. Czech. Chem. Commun., 58, 592 (1993).

    Article  CAS  Google Scholar 

  39. L. Wei, J. Xue, H. Liu, W. Wang, and Y. Li, Org. Lett., 14, 5302 (2012).

    Article  CAS  Google Scholar 

  40. Z. Shen and V. M. Dong, Angew. Chem., Int. Ed., 48, 784 (2009).

    Article  CAS  Google Scholar 

  41. Y. Hari, R. Kondo, K. Date, and T. Aoyama, Tetrahedron, 65, 8708 (2009).

    Article  CAS  Google Scholar 

  42. M. E. Dudley, M. M. Morshed, and M. M. Hossain, Synthesis, 1711 (2006).

  43. M. E. Dudley, M. M. Morshed, and M. M. Hossain, Org. Synth., 86, 172 (2009).

    Article  CAS  Google Scholar 

  44. E. Yoshioka, H. Tanaka, S. Kohtani, and H. Miyabe, Org. Lett., 15, 3938 (2013).

    Article  CAS  Google Scholar 

  45. N. Sakiyama, K. Noguchi, and K. Tanaka, Angew. Chem., Int. Ed., 51, 5976 (2012).

    Article  CAS  Google Scholar 

  46. B. Halton, C. S. Jones, and D. Margetic, Tetrahedron, 57, 3529 (2001).

    Article  CAS  Google Scholar 

  47. H. M. Godbolea, A. A. Ranadea, A. R. Josepha, and M. V. Paradkara, Synth. Commun., 30, 2951 (2000).

    Article  Google Scholar 

  48. P. J. Perry, V. H. Pavlidis, J. A. Hadfield, and I. G. C. Coutts, J. Chem. Soc., Perkin Trans. 1, 1085 (1995).

  49. P. J. Perry, V. H. Pavlidis, and J. A. Hadfield, Tetrahedron, 53, 3195 (1997).

    Article  CAS  Google Scholar 

  50. C. Wu, R. K. Johnson, M. R. Mattern, J. C. Wong, and D. G. I. Kingston, J. Nat. Prod., 62, 963 (1999).

    Article  CAS  Google Scholar 

  51. Y. Ohta, M. Doe, Y. Morimoto, and T. Kinoshita, J. Heterocycl. Chem., 37, 731 (2000).

    Article  CAS  Google Scholar 

  52. D. Qin, R. X. Ren, T. Siu, C. Zheng, and S. J. Danishefsky, Angew. Chem., Int. Ed., 40, 4709 (2001).

    Article  CAS  Google Scholar 

  53. J. Koyanagi, K. Yamamoto, K. Nakayama, and A. Tanaka, J. Heterocycl. Chem., 34, 407 (1997).

    Article  CAS  Google Scholar 

  54. S. M. Starling, D. S. Raslan, and A. B. de Oliveira, Synth. Commun., 28, 1013 (1998).

    Article  CAS  Google Scholar 

  55. S. M. Starling, D. S. Raslan, A. B. de Oliveira, and C. L. Zani, Synth. Commun., 28, 3567 (1998).

    Article  CAS  Google Scholar 

  56. V. V. Mel'chin, V. T. Abaev, A. V. Butin, and G. D. Krapivin, J. Heterocycl. Chem., 42, 1429 (2006).

    Article  Google Scholar 

  57. A. V. Butin, V. V. Mel'chin, V. T. Abaev, W. Bender, A. S. Pilipenko, and G. D. Krapivin, Tetrahedron, 62, 8045 (2006).

    Article  CAS  Google Scholar 

  58. A. V. Fin'ko, O. V. Serdyuk, and A. V. Butin, Khim. Geterotsikl. Soedin., 1040 (2012). [Chem. Heterocycl. Compd., 48, 969 (2012)].

  59. A. V. Butin, A. V. Fin'ko, E. V. Sudarkin, and F. A. Tsiunchik, Khim. Geterotsikl. Soedin.,776 (2011). [Chem. Heterocycl. Compd., 47, 477 (2011)].

  60. E. A. Anderson, E. J. Alexanian, and E. J. Sorensen, Angew. Chem., Int. Ed., 43, 1998 (2004).

    Article  CAS  Google Scholar 

  61. E. H. Sessions, R. T. O'Connor, Jr., and P. A. Jacobi, Org. Lett., 9, 3221 (2007).

    Article  CAS  Google Scholar 

  62. E. H. Sessions and P. A. Jacobi, Org. Lett., 8, 4125 (2006).

    Article  CAS  Google Scholar 

  63. E. O. Onyango and P. A. Jacobi, J. Org. Chem., 77, 7411 (2012).

    Article  CAS  Google Scholar 

  64. E. Burgueño-Tapia, M. A. Bucio, S. Rivera, and P. Joseph-Nathan, J. Nat. Prod., 64, 518 (2001).

    Article  Google Scholar 

  65. S.-L. Cui, X.-F. Lin, and Y.-G. Wang, Eur. J. Org. Chem., 5174 (2006).

  66. J. Einhorn, P. Demerseman, and R. Royer, J. Heterocycl. Chem., 22, 1243 (1985).

    Article  CAS  Google Scholar 

  67. V. V. Mel'chin and A. V. Butin, Tetrahedron Lett., 47, 4117 (2006).

    Article  Google Scholar 

  68. A. V. Fin'ko, V. O. Babikov, A. S. Pilipenko, V. T. Abaev, I. V. Trushkov, and A. V. Butin, Monatsh. Chem., 144, 1711 (2013).

    Article  Google Scholar 

  69. W. Adam, H. Hauer, T. Mosandi, C. R. Saha-Moller, W. Wagner, and D. Wild, Liebigs Ann. Chem., 1227 (1990).

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This work was carried out with the financial support of the Russian Federation Ministry of Education and Science in the framework of State Assignment to Higher Education Institutions (2515) and the Perm Krai Ministry of Education.

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Correspondence to A. V. Butin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 674-689, May, 2014.

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Uchuskin, M.G., Shcherbinin, V.A. & Butin, A.V. Synthesis and Transformations of Naphtho[2,3-B]Furans (Review). Chem Heterocycl Comp 50, 619–633 (2014). https://doi.org/10.1007/s10593-014-1515-2

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  • DOI: https://doi.org/10.1007/s10593-014-1515-2

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