Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Hexahydrofuro[2,3-b]furan and Hexahydrofuro[2,3-b]pyran Derivatives Starting from Baylis-Hillman Adducts via the Ueno-Stork Reaction

  • Gowrisankar, Saravanan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2006.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Roggenbuck, R.; Schmidt, A.; Eilbracht, P. Org. Lett. 2002, 4, 289 https://doi.org/10.1021/ol017083o
  2. Yanada, R.; Koh, Y.; Nishimori, N.; Matsumura, A.; Obika, S.; Mitsuya, H.; Fujii, N.; Takemoto, Y. J. Org. Chem. 2004, 69, 2417 https://doi.org/10.1021/jo035482m
  3. Kumari, G. N. K.; Balachandran, J.; Aravind, S.; Ganesh, M. R. J. Agric. Food Chem. 2003, 51, 1555 https://doi.org/10.1021/jf025920a
  4. Enomoto, M.; Nakahata, T.; Kuwahara, S. Tetrahedron 2006, 62, 1102 https://doi.org/10.1016/j.tet.2005.10.078
  5. Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron 2000, 56, 1745 https://doi.org/10.1016/S0040-4020(00)00060-0
  6. Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137 https://doi.org/10.1021/ja0032428
  7. Fujita, K.; Yorimitsu, H.; Oshima, K. Synlett 2002, 337
  8. Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627 https://doi.org/10.1016/S0040-4020(03)01016-0
  9. Hayashi, Y.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1988, 39, 63 https://doi.org/10.1016/S0040-4039(97)10489-0
  10. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouetard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233 https://doi.org/10.1021/jo0013655
  11. Sharma, G. V. M.; Krishnudu, K. Carbohydr. Res. 1995, 268, 287 https://doi.org/10.1016/0008-6215(94)00324-9
  12. Torii, S.; Inokuchi, T.; Yukawa, T. J. Org. Chem. 1985, 50, 5875 https://doi.org/10.1021/jo00350a090
  13. Kelly, D. R.; Picton, M. R. J. Chem. Soc., Perkin Trans. 1 2000, 1559
  14. Mayer, S.; Prandi, J. Tetrahedron Lett. 1996, 37, 3117 https://doi.org/10.1016/0040-4039(96)00505-9
  15. Morikawa, T.; Nishiwaki, T.; Iitaka, Y.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 671 https://doi.org/10.1016/S0040-4039(00)95809-X
  16. Rhode, O.; Hoffmann, H. M. R. Tetrahedron 2000, 56, 6479 https://doi.org/10.1016/S0040-4020(00)00592-5
  17. Hoffmann, H. M. R.; Herden, U.; Breithor, M.; Rhode, O. Tetrahedron 1997, 53, 8383 https://doi.org/10.1016/S0040-4020(97)00518-8
  18. Kelly, D. R.; Picton, M. R. J. Chem. Soc., Perkin Trans. 1 2000, 1571
  19. Inokuchi, T.; Kawafuchi, H. Synlett 2001, 421
  20. Mesmaeker, A. D.; Hoffmann, P.; Ernst, B. Tetrahedron Lett. 1988, 29, 6585 https://doi.org/10.1016/S0040-4039(00)82403-X
  21. Tenaglia, A.; Barille, D. Synlett 1995, 776
  22. Marco-Contelles, J. Chem. Commun. 1996, 2629
  23. Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374 https://doi.org/10.1021/ja0100423
  24. Salom-Roig, X. J.; Denes, F.; Renaud, P. Synthesis 2004, 1903
  25. Villar, F.; Equey, O.; Renaud, P. Org. Lett. 2000, 2, 1061 https://doi.org/10.1021/ol005613v
  26. Villar, F.; Renaud, P. Tetrahedron Lett. 1998, 39, 8655 https://doi.org/10.1016/S0040-4039(98)01971-6
  27. Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375 https://doi.org/10.1016/S0040-4039(99)00487-6
  28. Villar, F.; Kolly-Kovac, T.; Equey, O.; Renaud, P. Chem. Eur. J. 2003, 9, 1566 https://doi.org/10.1002/chem.200390180
  29. Corminboeuf, O.; Renaud, P.; Schiesser, C. H. Chem. Eur. J. 2003, 9, 1578 https://doi.org/10.1002/chem.200390181
  30. Horton, D.; Priebe, W.; Sznaidman, M. Carbohydr. Res. 1990, 205, 71 https://doi.org/10.1016/0008-6215(90)80129-Q
  31. Mayer, S.; Prandi, J.; Bamhaoud, T.; Bakkas, S.; Guillou, O. Tetrahedron 1998, 54, 8753 https://doi.org/10.1016/S0040-4020(98)00478-5
  32. Tatsuta, K.; Fujimoto, K.; Kinoshita, M.; Umezawa, S. Carbohydr. Res. 1977, 54, 85 https://doi.org/10.1016/S0008-6215(00)80558-3
  33. Bellucci, G.; Chiappe, C.; D'Andrea, F.; Lo Moro, G. Tetrahedron 1997, 53, 3417 https://doi.org/10.1016/S0040-4020(97)00064-1
  34. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2005, 46, 4859 https://doi.org/10.1016/j.tetlet.2005.05.057
  35. Park, D. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1440 https://doi.org/10.5012/bkcs.2005.26.9.1440
  36. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481 https://doi.org/10.5012/bkcs.2005.26.10.1481
  37. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564 https://doi.org/10.1021/ja00384a082
  38. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741 https://doi.org/10.1021/ja00349a082
  39. Dulcere, J.-P.; Agati, V.; Rodriguez, J. J. Chem. Soc., Chem. Commun. 1993, 1038
  40. Baguley, P. A.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 2073
  41. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 413 https://doi.org/10.5012/bkcs.2004.25.3.413

Cited by

  1. A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives vol.12, pp.37, 2014, https://doi.org/10.1039/C4OB00642A
  2. Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives vol.80, pp.2, 2015, https://doi.org/10.1021/jo502672x
  3. Copper(I)-Catalyzed Radical Cyclization vol.359, pp.3, 2017, https://doi.org/10.1002/adsc.201600895
  4. Synthesis of Hexahydrofuro[2,3-b]furan and Hexahydrofuro[2,3-b]pyran Derivatives Starting from Baylis—Hillman Adducts via the Ueno—Stork Reaction. vol.37, pp.52, 2006, https://doi.org/10.1002/chin.200652141
  5. An Expeditious Synthesis of Substituted Pyrrolidines and Tetrahydrofurans Starting from Baylis-Hillman Adducts vol.28, pp.10, 2006, https://doi.org/10.5012/bkcs.2007.28.10.1844
  6. Synthesis of Isochroman and Tetrahydroisoquinoline Derivatives from Baylis-Hillman Adducts by Radical Cyclization vol.28, pp.12, 2006, https://doi.org/10.5012/bkcs.2007.28.12.2501
  7. Facile Synthesis of 4-Substituted 3-Exo-methylenechroman Derivatives via Radical Cyclization Starting from Salicylaldehydes vol.28, pp.4, 2006, https://doi.org/10.5012/bkcs.2007.28.4.624
  8. Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks vol.64, pp.20, 2008, https://doi.org/10.1016/j.tet.2008.02.087
  9. Synthesis of Rearranged N-Tosyl Aza-Baylis-Hillman Adducts under Acidic Conditions Catalyzed by CH3SO3H or Montmorillonite K10 vol.30, pp.4, 2006, https://doi.org/10.5012/bkcs.2009.30.4.941