Diastereoselective synthesis of β-piperonyl-γ-butyrolactones from Morita-Baylis-Hillman adducts. highly efficient synthesis of (±)-yatein, (±)-podorhizol and (±)-epi-podorhizol

Journal of the Brazilian Chemical Society

Volumn 21, Issue 12, 2010, Pages 2327-2339

  Trazzi, Giordano ^a   André, Marcelo Fabiano ^a   Coelho, Fernando ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Diastereoselectivity; Lignans; Morita Baylis Hillman

Indexed keywords

EID: 78649712114     PISSN: 01035053     EISSN: 16784790     Source Type: Journal    
DOI: 10.1590/S0103-50532010001200021     Document Type: Article

References (115)

1. Ayres, D. C.; Loike, J. D. In Chemistry and Pharmacology of Natural Products: Lignans; Chemical, Biological and Clinical Properties; Cambridge University Press: New York, 1990;
2. Pan, J. -Y.; Chen, S. -L.; Yang, M. -H.; Wu, J.; Sinkkonen, J.; Zou, K.; Nat. Prod. Rep. 2009, 26, 1251.
3. Botta, B.; Monache, G. D.; Misiti, D.; Vitali, A.; Zappia, G.; Curr. Med. Chem. 2001, 8, 1363.
4. Cassady, J. M.; Anticancer Agents Based on Natural Product Models, Academic Press: New York, 1980;
5. MacRae, W. D.; Towers, G. H.; Phytochemistry 1984, 23, 1207;
6. Glinski, M. B.; Freed, J. C.; Durst, T. J.; J. Org. Chem. 1987, 52, 2749;
7. Figgitt, D. P.; Denyer, S. P.; Dewick, P. M.; Jackson, D. E.; Williams, P.; Biochem. Biophys. Res. Commun. 1989, 160, 257;
8. Mann, J.; Davidson, R. S.; Hobbs, J. B.; Banthorpe, D. V.; Harborne, J. B.; Natural Products: Their Chemistry and Biological Significance, Longman: Essex, U.K., 1994;
9. Kasper, R.; Ganer, D.; Doehmer, J.; Planta Med. 1994, 60, 441;
10. Middel, O.; Woerdenbag, H. J.; Uden, W. D.; Oeveren, A.; Jansen, J. F. G. A.; Feringa, B. L.; Konings, A. W. T.; Pras, N.; Kellog, R. M.; J. Med. Chem. 1995, 38, 2112;
11. Gordaliza, M.; Corral, M.; Castor, M. A.; Vazquez, M. L. L.; Garcia, P. A.; Feliciano, A. S.; Grávalos, M. D. G.; Bioorg. Med. Chem. Lett. 1995, 5, 2465;
12. Yang, L. M.; Lin, S. J.; Yang, T. S.; Lu, K. H.; Bioorg. Med. Chem. Lett. 1996, 6, 941;
13. Eich, E.; Pertz, H.; Kaloga, M.; Schulz, J.; Fesen, M. R.; Mazumder, A.; Pommier, Y.; J. Med. Chem. 1996, 39, 86;
14. Montanari, C. A.; Bolzani, V. S.; Quim. Nova 2001, 24, 105;
15. Yunes, R. A.; Pedrosa, R. C.; Filho, V. C.; Quim. Nova 2001, 24, 147;
16. Usia, T.; Watabe, T.; Kadota, S.; Tezuka, Y.; Life Sci. 2005, 76, 2381;
17. Adlercreutz, H.; Crit. Rev. Clin. Lab. Sci. 2007, 44, 483;
18. For an example of interaction lignans-insects, see: Harmatha, J.; Dinan, L.; Phytochem. Rev. 2003, 2, 321.
19. Tan, X. -Q.; Chen, H. -S.; Liu, R. -H.; Tan, C, -H.; Xu, C. -L.; Xuan, W. -D.; Zhang, W. -D.; Planta Med. 2005, 71, 93.
20. Nuntanakorn, P.; Jiang, B.; Einbond, L. S.; Yang, H.; Kronenberg, F.; Weinstein, I. B.; Kennelly, E. J.; J. Nat. Prod. 2006, 69, 314.
21. For the recent review about the synthesis of this type of lignans, see: Brown, R. C. D.; Swain, N. A.; Synthesis 2004, 811.
22. Li, Y. S.; Wang, Z. T.; Z. T.; Zhang, M.; Luo, S. D.; Chen, J. J.; Nat. Prod. Res. 2005, 19, 125.
23. Li, R. H.; Feng, Y. L.; Yang, Z. G.; Wang, J.; Daikonya, A.; Kitanaka, S.; Xu, L. Z.; Yang, S. L.; Chem. Pharm. Bull. 2006, 54, 1022;
24. Li, R. H.; Wang, L. Y.; Yang, Z. G.; Kitanaka, S.; J. Nat. Prod. 2007, 70, 1999.
25. Chen, J. J.; Chou, E. T.; Duh, C. Y.; Yang, S. Z.; Chen, I. S.; Planta Med. 2006, 72, 351.
26. Jardine, I. In Anticancer Agents based on Natural Products; Academic Press, New York, 1980;
27. Weiss, S. G.; Tin-Wa, M.; Perdue, R. E.; Farnsworth, N. R.; J. Pharm. Sci. 1975, 64, 95;
28. Sellars, J. D.; Steel, P. G.; Eur. J. Org. Chem. 2007, 3815;
29. Roulland, E.; Magiatis, P.; Arimondo, P.; Bertounesque, E.; Monneret, C.; Bioorg. Med. Chem. 2002, 10, 3463;
30. For the use of this type of lignans as lead compound, see: Apers, S.; Vlietinck, A.; Pieters, L.; Phytochem. Rev. 2003, 2, 201.
31. Wagner, H.; In Natural Products as Medicinal Agents; Beal, J. L.; Reinheard E., eds.; Hippocrates Verlag: Stuttgart, 1981, p. 217;
32. Ward, R. S.; Chem. Soc. Rev. 1982, 75;
33. Whiting, D. A.; Nat. Prod. Rep. 1985, 2, 191;
34. Whiting, D. A.; Nat. Prod. Rep. 1987, 4, 499;
35. Whiting, D. A.; Nat. Prod. Rep. 1990, 7, 349;
36. Ward, R. S.; Tetrahedron 1990, 46, 5029;
37. Ward, R. S.; Synthesis 1992, 719;
38. Ward, R. S.; Nat. Prod. Rep. 1993, 10, 1;
39. Lee, K. H.; Wang, H. K.; J. Food Drug Anal. 1995, 3, 209;
40. Ward, R. S.; Nat. Prod. Rep. 1995, 12, 183;
41. Ward, R. S.; Nat. Prod. Rep. 1997, 14, 43;
42. Ward, R. S.; Nat. Prod. Rep. 1999, 16, 75;
43. Zhu, X. K.; Guan, J.; Tachibana, Y.; Bastow, K. F.; Cho, S. J.; Cheng, H. H.; Cheng, Y. C.; Gurwith, M.; Lee, K. H.; J. Med. Chem. 1999, 42, 2441;
44. Sefkow, M.; Raschke, M.; Steiner, C.; Pure Appl. Chem. 2003, 75, 273;
45. Da Silva, R.; Pedersoli, R.; Lacerda, V.; Donate, P. M.; de Albuquerque, S.; Bastos, J. K.; Araujo, A. L. S. D.; Silva, M. L. A. E.; Magn. Reson. Chem. 2005, 43, 966;
46. Da Silva, R.; de Souza, G. H. B.; da Silva, A. A.; de Souza, V. A.; Pereira, A. C.; Royo, V. A.; Silva, M. L. A.; Donate, P. M.; Araujo. A. L. S. M.; Carvalho, J. C. T.; Bastos, J. K.; Bioorg. Med. Chem. Lett. 2005, 15, 1033;
47. Donate, P. M.; Frederico, D.; da Silva, R.; Constantino, M. G.; Del Ponte, G.; Bonatto, P. S.; Tetrahedron: Asymmetry 2003, 14, 3253.
48. Edlin, C. D.; Faulkner, J.; Helliwell, M.; Knight, C. K.; Parker, J.; Quayle, P.; Raftery, J.; Tetrahedron 2006, 62, 3004;
49. Koul, S.; Singh, B.; Taneja, S. C.; Qazi, G. N.; Tetrahedron 2003, 59, 3487;
50. Verza, M.; Arakawa, N. S.; Lopes, N. B.; Kato, M. J.; Pupo, M. T.; Said, S.; Carvalho, I.; J. Braz. Chem. Soc. 2009, 20, 195;
51. Marchesini, A. M.; Prado, G. G.; Messiano, G. B.; Machado, M. B.; Lopes, L. M. X.; J. Braz. Chem. Soc. 2009, 20, 1598;
52. Morais, S. K. R.; Teixeira, A. F.; Torres, Z. E. S.; Nunomura, S. M.; Kanashiro, E. H. Y.; Lindoso, J. A. L.; Yoshida, M.; J. Braz. Chem. Soc. 2009, 20, 1110;
53. Fernandes, C. C.; Vieira, P. C.; da Silva, V. C.; Dall'Oglio, E. L.; da Silva, L. E.; de Sousa Jr., P. T.; J. Braz. Chem. Soc. 2009, 20, 379.
54. Enders, D.; Lausberg, V.; Del Signore, G.; Berner, O. M.; Synthesis 2002, 515.
55. Edlin, C. D.; Faulkner, J.; Helliwell, M.; Knight, C. K.; Parker, J.; Quayle, P.; Raftery, J.; Tetrahedron 2006, 62, 3004;
56. Hidemi, Y.; Suzuki, Y.; Matsuura, D.; Takabe, K.; Heterocycles 2005, 65, 519;
57. Masunari, A.; Ishida, E.; Trazzi, G.; Almeida, W. P.; Coelho, F.; Synth. Commun. 2001, 31, 2127;
58. Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 1998, 39, 8609;
59. Boissin, P.; Dhal, R.; Brown, E.; J. Chem. Res. (S) 1991, 332;
60. Ishiguro, T.; Mizuguchi, H.; Tomioka, K.; Koga, K.; Chem. Pharm. Bull. 1985, 33, 609;
61. Lewis, S. N.; Popper, T. L.; Tetrahedron 1967, 23, 4197.
62. For some leading references concerning the Morita-Baylis-Hillman reaction see: Basavaiah, D.; Rao, K. V.; Reddy, R.; J. Chem. Soc. Rev. 2007, 36, 1581;
63. Singh, V.; Batra, S.; Tetrahedron 2008, 64, 4511;
64. Almeida, W. P.; Coelho, F.; Quim. Nova 2001, 23, 98.
65. For new insights about the mechanism of this reaction, see: Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N.; Angew. Chem., Int. Ed. 2004, 43, 4330;
66. Santos, L. S.; da Silveira Neto, B. A.; Consorti, C. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Dupont, J.; Eberlin, M. N.; J. Phys. Org. Chem. 2006, 19, 731;
67. Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C.; Angew. Chem., Int. Ed. 2005, 44, 1706;
68. Robiette, R.; Aggarwal, V. K.; Harvey, J. N.; J. Am. Chem. Soc. 2007, 129, 15513;
69. Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T.; Org. Lett. 2005, 7, 147;
70. Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T.; J. Org. Chem. 2005, 70, 3980;
71. Roy, D.; Sunoj, R. B.; Org. Lett. 2007, 9, 4873;
72. Amarante, G. W.; Milagre, H. M. S.; Vaz, B. G.; Ferreira, B. R. V.; Eberlin, M. N.; Coelho, F.; J. Org. Chem. 2009, 74, 3031;
73. Amarante, G. W.; Benassi, M.; Milagre, H. M. S.; Braga, A. A. C.; Maseras, F.; Eberlin, M. N.; Coelho, F.; Chem. Eur. J. 2009, 15, 12460.
74. For some outstanding examples concerning the use of Morita-Baylis-Hillman as substrate for natural products and drugs synthesis, see: Amarante, G. W.; Cavallaro, M.; Coelho, F.; Tetrahedron Lett. 2010, 51, 2597;
75. Amarante, G. W.; Benassi, M.; Pascoal, R. N.; Eberlin, M. N.; Coelho, F.; Tetrahedron 2010, 66, 4370;
76. Ferreira, M.; Fernandes, L.; Sá, M. M. M.; J. Braz. Chem. Soc. 2009, 30, 564;
77. Amarante, G. W.; Rezende, P.; Cavallaro, M.; Coelho, F.; Tetrahedron Lett. 2008, 49, 3744;
78. Coelho, F.; Veronese, D.; Pavam, C. H.; de Paula, V. I.; Buffon, R.; Tetrahedron 2006, 62, 4563;
79. Perez, R.; Veronese, D.; Coelho, F.; Antunes, O. A. C.; Tetrahedron Lett. 2006, 47, 1325;
80. Silveira, G. P. D.; Coelho, F.; Tetrahedron Lett. 2005, 46, 6477;
81. Reddy, L. J; Fournier, J. F; Reddy, B.V. S; Corey; E. J.; Org. Lett. 2005, 7, 2699;
82. Almeida, W. P.; Coelho, F.; Tetrahedron Lett. 2003, 44, 937;
83. Feltrin, M. A.; Almeida, W. P.; Synth. Commun. 2003, 33, 1141;
84. Dunn, P. J.; Fournier, J. F; Hughes, M. L.; Searle, P. M.; Wood, A. S.; Org. Process Res. Dev. 2003, 7, 244;
85. Rossi, R. C.; Coelho, F.; Tetrahedron Lett. 2002, 42, 2797;
86. Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P.; Tetrahedron 2001, 57, 6901;
87. Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S.; Chem. Commun. 2001, 2030;
88. Mateus, C. R.; Coelho, F.; J. Braz. Chem. Soc. 2005, 16, 386;
89. McCauley, J. A.; Nagasawa, K.; Lander, P. A; Mischke, S. G.; Semones, M. A.; Kishi, Y.; J. Am. Chem. Soc. 1998, 120, 7647;
90. Coelho, F.; Depres, J. P.; Brocksom, T. J.; Greene, A. E.; Tetrahedron Lett. 1989, 30, 565.
91. Harmatha, J.; Nawrot, J.; Entomol. Exp. Appl. 2002, 104, 51.
92. Kuo, Y. -C.; Kuo, Y. -H.; Lin, Y. -L.; Tsai, W. -J.; Antiviral Res. 2006, 70, 112.
93. Ito, C.; Itoigawa, M.; Ogata, M.; Mou, X. Y.; Tokuda, H.; Nishino, H.; Furukawa, H.; Planta Med. 2001, 67, 166.
94. Heinrich, M.; Curr. Top. Med. Chem. 2003, 3, 29.
95. More, J. D.; Finney, N. S.; Org. Lett. 2002, 4, 17, 3001.
96. Katritzky, A. R.; Duell, B. L.; Durst, H. D.; Knier, B.; Tetrahedron Lett. 1987, 28, 3899;
97. Kaluza, Z.; Mostowicz, D.; Dolega, G.; Wojcik, R.; Tetrahedron 2008, 64, 2321.
98. Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P.; J. Org. Chem. 1996, 61, 566;
99. Pilli, R. A.; Andrade, C. K. Z.; Souto, C. R O. Meijere, A.; J. Org. Chem. 1998, 63, 7811.
100. Abella, C. A. M.; Rezende, P.; Lino de Souza, M. F.; Coelho, F.; Tetrahedron Lett. 2008, 49, 145;
101. Liao, M.; Yao, W.; Wang, J.; Synthesis 2004, 2633 and references cited therein.
102. Fujita, M.; Hyama, T.; J. Org. Chem. 1988, 53, 5405;
103. Fujita, M.; Hiyama, T.; J. Am. Chem. Soc. 1984, 106, 4629;
104. Corriu, R. J. P.; Perz, R.; Reye, C.; Tetrahedron 1983, 39, 999;
105. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C.; J. Organomet. Chem. 1979, 172, 143.
106. It is well known that the reduction of carbonyl compounds with NaBH4 in 2-propanol is very slow. We test this experimental condition in order to improve the diastereoselectivity we have attained with methanol. Unfortunately, the diastereoselective ratio was poorer. Most probably this result should be due to the moderate solubility of our ketoesters in 2-propanol. To some comments concerning the reduction of carbonyl compounds with NaBH4 in different solvents, see: Brown, H. C.; Mead, E. J.; Subba Rao, B. C.; J. Am. Chem. Soc. 1955, 75, 6209;
107. Brown, M. S.; Rapoport, H.; J. Org. Chem. 1963, 28, 3261.
108. Ley, S. V.; Norman, J.; Griffith, W. P.; Mardsen, S. P.; Synthesis 1994, 639;
109. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D.; Chem. Commun. 1987, 1625.
110. 4, followed by the treatment with HBr in 62% yield for two steps.
111. Neidigh, K. A.; Kingston, D. G. I.; Lewis, N. G.; J. Nat. Prod. 1994, 57, 891.
112. Yamauchi, S.; Machi, M.; Kinoshita, Y.; Biosci., Biotechnol., Biochem. 1999, 63, 1453;
113. Kamil, W. M.; Dewick, P. M.; Phytochemistry 1986, 25, 2093;
114. San Feliciano, A.; Medarde, M.; Lopez, J. L.; Puebla, P.; del Corral, J. M. M.; Barrero, A. F.; Phytochemistry 1989, 28, 2863;
115. Ziegler, F. E.; Schwartz, J. A.; J. Org. Chem. 1978, 43, 985.