Bulletin of the Korean Chemical Society

  • 제30권5호
  • /
  • Pages.1012-1020
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Expedient One-Pot Synthesis of γ-hydroxybutenolides Starting from Baylis-Hillman Adducts: Lactonization, Isomerization, and Aerobic Oxidation of α-Methylene-γ-hydroxyester

  • Kim, Ko-Hoon (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyun-Seung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Sung-Hwan (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) ;
  • Lee, Ji-Eun (Department of Chemistry (BK21) and Central Instrument Facility, Gyeongsang National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • 발행 : 2009.05.20
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초록

We developed an efficient three-step synthetic protocol of $\gamma$-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot $K_2CO_3$-mediated synthesis of $\gamma$-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.

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참고문헌

  1. Cheung, A. K.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 11584-11585 https://doi.org/10.1021/ja026899x
  2. Magnuson, S. R.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 1615-1616 https://doi.org/10.1021/ja9740428
  3. Basabe, P.; Delgado, S.; Marcos, I. S.; Diez, D.; Diego, A.; de Roman, M.; Sanz, F.; Urones, J. G. Tetrahedron 2007, 63, 8939-8948 https://doi.org/10.1016/j.tet.2007.06.004
  4. Basabe, P.; Delgado, S.; Marcos, I. S.; Diez, D.; Diego, A.; De Roman, M.; Urones, J. G. J. Org. Chem. 2005, 70, 9480-9485 https://doi.org/10.1021/jo0515529
  5. Marcos, I. S.; Escola, M. A.; Moro, R. F.; Basabe, P.; Diez, D.; Sanz, F.; Mollinedo, F.; de la Iglesia- Vicente, J.; Sierra, B. G.; Urones, J. G. Bioorg. Med. Chem. 2007, 15, 5719-5737 https://doi.org/10.1016/j.bmc.2007.06.007
  6. Guerrero, M. D.; Aquino, M.; Bruno, I.; Terencio, M. C.; Paya, M.; Riccio, R.; Gomez-Paloma, L. J. Med. Chem. 2007, 50, 2176-2184 https://doi.org/10.1021/jm0700823
  7. Ma, S.; Wu, B.; Shi, Z. J. Org. Chem. 2004, 69, 1429-1431 https://doi.org/10.1021/jo0355698
  8. Ma, S.; Wu, B.; Ma, Z. Faming Zhuanli Shenqing Gongkai Shumingshu 2004, CN 1526709A (Chem. Abstr. 143, 97252)
  9. Holtke, C.; Law, M. P.; Wagner, S.; Breyholz, H.-J.; Kopka, K.; Bremer, C.; Levkau, B.; Schober, O.; Schafers, M. Bioorg. Med. Chem. 2006, 14, 1910-1917 https://doi.org/10.1016/j.bmc.2005.10.039
  10. Padakanti, S.; Veeramaneni, V. R.; Pattabiraman, V. R.; Pal, M.; Yeleswarapu, K. R. Tetrahedron Lett. 2002, 43, 8715-8719 https://doi.org/10.1016/S0040-4039(02)02144-5
  11. Liu, H.-M.; Zhang, F.; Zhang, J.; Li, S. Carbohydr. Res. 2003, 338, 1737-1743 https://doi.org/10.1016/S0008-6215(03)00257-X
  12. Gudipati, V.; Curran, D. P.; Wilcox, C. S. J. Org. Chem. 2006, 71, 3599-3607 https://doi.org/10.1021/jo060217x
  13. Patt, W. C.; Edmunds, J. J.; Repine, J. T.; Berryman, K. A.; Reisdorph, B. R.; Lee, C.; Plummer, M. S.; Shahripour, A.; Haleen, S. J.; Keiser, J. A.; Flynn, M. A.; Welch, K. M.; Reynolds, E. E.; Rubin, R.; Tobias, B.; Hallak, H.; Doherty, A. M. J. Med. Chem. 1997, 40, 1063-1074 https://doi.org/10.1021/jm9606507
  14. Patil, S. N.; Liu, F. J. Org. Chem. 2007, 72, 6305-6308 https://doi.org/10.1021/jo070666c
  15. Patil, S. N.; Liu, F. Org. Lett. 2007, 9, 195-198 https://doi.org/10.1021/ol062551l
  16. Aquino, M.; Bruno, I.; Riccio, R.; Gomez-Paloma, L. Org. Lett. 2006, 8, 4831-4834 https://doi.org/10.1021/ol0618611
  17. Paquette, L. A.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4301-4304 https://doi.org/10.1016/S0040-4039(99)00781-9
  18. Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1489-1492 https://doi.org/10.5012/bkcs.2006.27.9.1489
  19. Lee, A. S.-Y.; Chang, Y.-T.; Wang, S.-H.; Chu, S.-F. Tetrahedron Lett. 2002, 43, 8489-8492 https://doi.org/10.1016/S0040-4039(02)02088-9
  20. Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2005, 46, 4209-4211 https://doi.org/10.1016/j.tetlet.2005.04.055
  21. Kabalka, G. W.; Venkataiah, B.; Chen, C. Tetrahedron Lett. 2006, 47, 4187-4189 https://doi.org/10.1016/j.tetlet.2006.04.063
  22. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325-7328 https://doi.org/10.1016/j.tetlet.2005.08.140
  23. Reid, C. S.; Zhang, Y.; Li, C.-J. Org. Biomol. Chem. 2007, 5, 3589-3591 https://doi.org/10.1039/b713244c
  24. Yu, S. H.; Ferguson, M. J.; McDonald, R.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 12808-12809 https://doi.org/10.1021/ja054171l
  25. Ramachandran, P. V.; Garner, G.; Pratihar, D. Org. Lett. 2007, 9, 4753-4756 https://doi.org/10.1021/ol702079f
  26. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891 https://doi.org/10.1021/cr010043d
  27. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350
  28. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062 https://doi.org/10.1016/0040-4020(96)00154-8
  29. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645 https://doi.org/10.2174/1385272023374094
  30. Lee, K. Y.; Gowrisankar, S.; Kim, J. N.Bull. Korean Chem. Soc. 2005, 26, 1481-1490 https://doi.org/10.5012/bkcs.2005.26.10.1481
  31. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574 and further references cited therein https://doi.org/10.1016/j.tet.2008.02.087
  32. Gowrisankar, S.; Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1670-1673 https://doi.org/10.1016/j.tetlet.2007.12.133
  33. Kim, J. M.; Kim, K. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3248-3251 https://doi.org/10.1016/j.tetlet.2008.03.102
  34. Gowrisankar, S.; Lee, H. S.; Lee, K. Y.; Lee,J.-E.; Kim, J. N. Tetrahedron Lett. 2007, 48, 8619-8622 https://doi.org/10.1016/j.tetlet.2007.10.043
  35. Lee, H. S.; Kim, S. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1773-1776 https://doi.org/10.1016/j.tetlet.2008.01.058
  36. Kim, S. H.; Kim, K. H.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1948-1951 https://doi.org/10.1016/j.tetlet.2008.01.110
  37. Lee, H. S.; Kim, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron 2008, 64, 2397-2404 https://doi.org/10.1016/j.tet.2008.01.001
  38. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325-7328 and the compound 5a was reported, see: https://doi.org/10.1016/j.tetlet.2005.08.140
  39. Shindo, M.; Yoshikawa, T.; Itou, Y.; Mori, S.; Nishii, T.; Shishido, K. Chem. Eur. J. 2006, 12, 524-536 https://doi.org/10.1002/chem.200500574
  40. Ma, S.; Shi, Z. Chem. Commun., 2002, 540-541
  41. Delaunay, J.; Orliac-Le Moing, A.; Simonet, J. Tetrahedron 1988, 44, 7089-7094 https://doi.org/10.1016/S0040-4020(01)86077-4
  42. Black, W. C.; Brideau, C.; Chan, C.-C.; Charleson, S.; Cromlish, W.; Gordon, R.; Grimm, E. L.; Hughes, G.; Leger, S.; Li, C.-S.; Riendeau, D.; Therien, M.; Wang, Z.; Xu, L.-J.; Prasit, P. Bioorg. Med. Chem. Lett. 2003, 13, 1195-1198 https://doi.org/10.1016/S0960-894X(03)00046-5
  43. Peters, R.; Althaus, M.; Nagy, A.-L. Org. Biomol. Chem. 2006, 4, 498-509 https://doi.org/10.1039/b514147h
  44. Watanabe, T.; Ishikawa, T. Tetrahedron Lett. 1999, 40, 7795-7798 https://doi.org/10.1016/S0040-4039(99)01618-4
  45. Iesce, M. R.; Cermola, F.; De Lorenzo, F.; Orabona, I.; Graziano, M. L. J. Org. Chem. 2001, 66, 4732-4735 https://doi.org/10.1021/jo0102112
  46. Schobert, R.; Stehle, R.; Milius, W. J. Org. Chem. 2003, 68, 9827-9830 https://doi.org/10.1021/jo030270a
  47. Iesce, M. R.; Graziano, M. L.; Cermola, F.; Scarpati, R. J. Chem. Soc., Chem. Commun. 1991, 1061-1062
  48. Sulikowski, G. A.; Agnelli, F.; Corbett, R. M. J. Org. Chem. 2000, 65, 337-342 https://doi.org/10.1021/jo9911286
  49. Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R. J. Org. Chem. 2004, 69, 9100-9108 https://doi.org/10.1021/jo0488053
  50. Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052 https://doi.org/10.1021/ol035022f
  51. Bagal, S. K.; Adlington, R. M.; Marquez, R.; Cowley, A. R.; Baldwin, J. E. Tetrahedron Lett. 2003, 44, 4993-4996 https://doi.org/10.1016/S0040-4039(03)01172-9
  52. Ma, S.; Yu, Z. Org. Lett. 2003, 5, 1507-1510. (f) Coperet, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422-3431 https://doi.org/10.1021/ja00117a011
  53. Coperet, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422-3431 https://doi.org/10.1021/ja00117a011
  54. Ospina, C. A.; Rodriguez, A. D.; Sanchez, J. A.; Ortega-Barria, E.; Capson, T. L.; Mayer, A. M. S. J. Nat. Prod. 2005, 68, 1519-1526 https://doi.org/10.1021/np050239z
  55. Kupchan, S. M.; Aynehchi, Y.; Cassady, J. M.; Schnoes, H. K.; Burlingame, A. L. J. Org. Chem. 1969, 34, 3867-3875 https://doi.org/10.1021/jo01264a028
  56. Okano, T.; Chokai, M.; Eguchi, S.; Hayakawa, Y. Tetrahedron 2000, 56, 6219-6222 https://doi.org/10.1016/S0040-4020(00)00581-0
  57. Ma, S.; Lu, L.; Lu, P. J. Org. Chem. 2005, 70, 1063-1065 https://doi.org/10.1021/jo048430l
  58. Khim, S.-K.; Dai, M.; Zhang, X.; Chen, L.; Pettus, L.; Thakkar, K.; Schultz, A. G. J. Org. Chem. 2004, 69, 7728-7733 https://doi.org/10.1016/S0040-4020(00)00581-0
  59. Franck, X.; Figadere, B. Tetrahedron Lett. 2002, 43, 1449-1451 https://doi.org/10.1021/jo048430l
  60. Shieh, W.-C.; Dell, S.; Repic, O. J. Org. Chem. 2002, 67, 2188-2191 https://doi.org/10.1021/jo0490853

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