Expedient one-pot synthesis of γ-hydroxybutenolides starting from Baylis-Hillman adducts: Lactonization, isomerization, and aerobic oxidation of α-methylene-γ-hydroxyester

Bulletin of the Korean Chemical Society

Volumn 30, Issue 5, 2009, Pages 1012-1020

  Kim, Ko Hoon ^a   Lee, Hyun Seung ^a   Kim, Sung Hwan ^a   Lee, Ka Young ^a   Lee, Ji Eun ^b   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b Gyeongsang National University   (South Korea)

Author keywords

Hydroxybutenolides; Baylis Hillman adducts; Hydroxylation; Lactones

Indexed keywords

AEROBIC OXIDATIONS; BAYLIS-HILLMAN ADDUCTS; BUTENOLIDES; CONJUGATE ADDITION REACTIONS; LACTONES; LACTONIZATION; ONE POT; ONE-POT SYNTHESIS; SYNTHETIC PROTOCOLS;

ADDITION REACTIONS; AROMATIC HYDROCARBONS; HYDROCARBONS; HYDROXYLATION;

SYNTHESIS (CHEMICAL);

EID: 70349733540     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.5.1012     Document Type: Article

References (73)

1. Cheung, A. K.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 11584-11585.
2. Magnuson, S. R.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 1615-1616.
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.
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.
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.
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 and further references cited therein.
7. For some recent synthesis of γ-hydroxybutenolides, see
8. Ma, S.; Wu, B.; Shi, Z. J. Org. Chem. 2004, 69, 1429-1431.
9. Ma, S.; Wu, B.; Ma, Z. Faming Zhuanli Shenqing Gongkai Shumingshu 2004, CN 1526709A (Chem. Abstr. 143, 97252).
10. 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.
11. Padakanti, S.; Veeramaneni, V. R.; Pattabiraman, V. R.; Pal, M.; Yeleswarapu, K. R. Tetrahedron Lett. 2002, 43, 8715-8719.
12. Liu, H.-M.; Zhang, F.; Zhang, J.; Li, S. Carbohydr. Res. 2003, 338, 1737-1743.
13. Gudipati, V.; Curran, D. P.; Wilcox, C. S. J. Org. Chem. 2006, 71, 3599-3607.
14. 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.
15. For the synthesis of γ-hydroxybutenolides from furans, see
16. Patil, S. N.; Liu, F. J. Org. Chem. 2007, 72, 6305-6308.
17. Patil, S. N.; Liu, F. Org. Lett. 2007, 9, 195-198.
18. Aquino, M.; Bruno, I.; Riccio, R.; Gomez-Paloma, L. Org. Lett. 2006, 8, 4831-4834.
19. For the synthesis of α-methylene-γ-butyrolactones, see
20. Paquette, L. A.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4301-4304.
21. Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1489-1492.
22. Lee, A. S.-Y.; Chang, Y.-T.; Wang, S.-H.; Chu, S.-F. Tetrahedron Lett. 2002, 43, 8489-8492.
23. Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2005, 46, 4209-4211.
24. Kabalka, G. W.; Venkataiah, B.; Chen, C. Tetrahedron Lett. 2006, 47, 4187-4189.
25. (f) Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325-7328.
26. Reid, C. S.; Zhang, Y.; Li, C.-J. Org. Biomol. Chem. 2007, 5, 3589-3591.
27. Yu, S. H.; Ferguson, M. J.; McDonald, R.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 12808-12809.
28. Ramachandran, P. V.; Garner, G.; Pratihar, D. Org. Lett. 2007, 9, 4753-4756.
29. For the general review on Baylis-Hillman chemistry, see
30. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.
31. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
32. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062.
33. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645.
34. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490.
35. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574 and further references cited therein.
36. For our recent contributions in Baylis-Hillman chemistry, see
37. Gowrisankar, S.; Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1670-1673.
38. Kim, J. M.; Kim, K. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3248-3251.
39. Gowrisankar, S.; Lee, H. S.; Lee, K. Y.; Lee, J.-E.; Kim, J. N. Tetrahedron Lett. 2007, 48, 8619-8622.
40. Lee, H. S.; Kim, S. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1773-1776.
41. Kim, S. H.; Kim, K. H.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1948-1951.
42. Lee, H. S.; Kim, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron 2008, 64, 2397-2404.
43. For the isomerization of double bond under catalytic hydrogenation conditions, see
44. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325-7328 and the compound 5a was reported, see
45. Shindo, M.; Yoshikawa, T.; Itou, Y.; Mori, S.; Nishii, T.; Shishido, K. Chem. Eur. J. 2006, 12, 524-536.
46. Ma, S.; Shi, Z. Chem. Commun., 2002, 540-541.
47. Delaunay, J.; Orliac-Le Moing, A.; Simonet, J. Tetrahedron 1988, 44, 7089-7094.
48. For the base-promoted aerobic oxidation process in a similar system, see
49. 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.
50. Peters, R.; Althaus, M.; Nagy, A.-L. Org. Biomol. Chem. 2006, 4, 498-509.
51. Watanabe, T.; Ishikawa, T. Tetrahedron Lett. 1999, 40, 7795-7798.
52. For the similar hydroperoxides formation, see
53. Iesce, M. R.; Cermola, F.; De Lorenzo, F.; Orabona, I.; Graziano, M. L. J. Org. Chem. 2001, 66, 4732-4735.
54. Schobert, R.; Stehle, R.; Milius, W. J. Org. Chem. 2003, 68, 9827-9830.
55. Iesce, M. R.; Graziano, M. L.; Cermola, F.; Scarpati, R. J. Chem. Soc., Chem. Commun. 1991, 1061-1062.
56. For the synthesis of butenolide-butyrolactone and butenolide dimeric compounds, see
57. Sulikowski, G. A.; Agnelli, F.; Corbett, R. M. J. Org. Chem. 2000, 65, 337-342.
58. Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R. J. Org. Chem. 2004, 69, 9100-9108.
59. Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052.
60. Bagal, S. K.; Adlington, R. M.; Marquez, R.; Cowley, A. R.; Baldwin, J. E. Tetrahedron Lett. 2003, 44, 4993-4996.
61. Ma, S.; Yu, Z. Org. Lett. 2003, 5, 1507-1510.
62. Coperet, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422-3431.
63. 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.
64. Kupchan, S. M.; Aynehchi, Y.; Cassady, J. M.; Schnoes, H. K.; Burlingame, A. L. J. Org. Chem. 1969, 34, 3867-3875.
65. 2 = 0.1117 (I > 2σ(I)). We omitted hydrogen atoms for clarity (Figure 1). The X-ray data has been deposited in CCDC with number 684684.
66. 2 = 0.1188 (I > 2σ(I)). We omitted hydrogen atoms for clarity (Figure 1). The X-ray data has been deposited in CCDC with number 684685.
67. For the Michael type self-dimerization and intermolecular Michael addition reactions of butenolides, see
68. Okano, T.; Chokai, M.; Eguchi, S.; Hayakawa, Y. Tetrahedron 2000, 56, 6219-6222.
69. For the synthesis of carbon-chain substituted butenolides, see
70. Ma, S.; Lu, L.; Lu, P. J. Org. Chem. 2005, 70, 1063-1065.
71. Khim, S.-K.; Dai, M.; Zhang, X.; Chen, L.; Pettus, L.; Thakkar, K.; Schultz, A. G. J. Org. Chem. 2004, 69, 7728-7733.
72. Franck, X.; Figadere, B. Tetrahedron Lett. 2002, 43, 1449-1451.
73. Shieh, W.-C.; Dell, S.; Repic, O. J. Org. Chem. 2002, 67, 2188-2191.