Synthesis and biological activity of lamellarin alkaloids: An overview

Heterocycles

Volumn 83, Issue 3, 2011, Pages 491-529

  Fukuda, Tsutomu ^a   Ishibashi, Fumito ^a   Iwaob, Masatomo ^b  

^a Chiba University   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952264809     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/REV-10-686     Document Type: Review

References (117)

1. Y. Nakao and N. Fusetani, J. Nat. Prod., 2007, 70, 689.
2. R. J. Andersen, D. J. Faulkner, H. Cun-Heng, G. D. Van Duyne, and J. Clardy, J. Am. Chem. Soc., 1985, 107, 5492.
3. N. Lindquist, W. Fenical, G. D. Van Duyne, and J. Clardy, J. Org. Chem., 1988, 53, 4570.
4. A. R. Carroll, B. F. Bowden, and J. C. Coll, Aust. J. Chem., 1993, 46, 489.
5. S. Urban, M. S. Butler, and R. J. Capton, Aust. J. Chem., 1994, 47, 1919.
6. S. Urban, L. Hobbs, J. N. A. Hooper, and R. J. Capton, Aust. J. Chem., 1995, 48, 1491.
7. S. Urban and R. J. Capton, Aust. J. Chem., 1996, 49, 711.
8. M. V. R. Reddy, D. J. Faulkner, Y. Venkateswarlu, and M. R. Rao, Tetrahedron, 1997, 53, 3457.
9. C. L. Cantrell, A. Groweiss, K. R. Gustafson, and M. R. Boyd, Nat. Prod. Lett., 1999, 14, 39.
10. R. A. Davis, A. R. Carroll, G. K. Pierens, and R. J. Quinn, J. Nat. Prod., 1999, 62, 419.
11. M. V. R. Reddy, M. R. Rao, D. Rhodes, M. S. T. Hansen, K. Rubins, F. D. Bushman, Y. Venkateswarlu, and D. J. Faulkner, J. Med. Chem., 1999, 42, 1901.
12. J. Ham and H. Kang, Bull. Korean Chem. Soc., 2002, 23, 163.
13. P. Krishnaiah, V. L. N. Reddy, G. Venkataramana, K. Ravinder, M. Srinivasulu, T. V. Raju, K. Ravikumar, D. Chandrasekar, S. Ramakrishna, and Y. Venkateswarlu, J. Nat. Prod., 2004. 67, 1168.
14. S. M. Reddy, M. Srinivasulu, N. Satyanarayana, A. K. Kondapi, and Y. Venkateswarlu, Tetrahedron, 2005, 61, 9242.
15. Lamellarin numbering utilized in this review follows the initial report by Faulkner
16. A. R. Quesada, M. D. G. Grávalos, and J. L. F. Puentes, Br. J. Cancer, 1996, 74, 677.
17. For reviews, see: (a) P. Cironi, F. Albericio, and M. Álvarez, Progress in Heterocyclic Chemistry, 2004, 16, 1;
18. C. Bailly, Curr. Med. Chem. - Anti-Cancer Agents, 2004, 4, 363;
19. S. T. Handy and Y. Zhang, Org. Prep. Proced. Int., 2005, 8, 411;
20. H. Fan, J. Peng, M. T. Hamann, and J.-F. Hu, Chem. Rev., 2008, 108, 264;
21. D. Pla, F. Albericio, and M. Álvarez, Anti-Cancer Agents in Med. Chem., 2008, 8, 746;
22. J. Kluza, P. Marchetti, and C. Bailly, 'Modern Alkaloids: Structure, Isolation, Synthesis and Biology,' ed. by E. Fattorusso and O. Taglialatela-Scafati, Wiley-VCH, Weinheim, 2008, pp. 171-187.
23. For a review on the synthesis of indolizine and related heterocycles including pyrrolo[2,1-a]isoquinoline
24. T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
25. F. Ishibashi, Y. Miyazaki, and M. Iwao, Tetrahedron, 1997, 53, 5951.
26. M. Iwao and T. Kuraishi, Bull. Chem. Soc. Jpn., 1980, 53, 297.
27. F. Ishibashi, S. Tanabe, T. Oda, and M. Iwao, J. Nat. Prod., 2002, 65, 500.
28. M. Banwell, B. Flynn, and D. Hockless, Chem. Commun., 1997, 2259.
29. P. Cironi, I. Manzanares, F. Albericio, and M. Álvarez, Org. Lett., 2003, 5, 2959.
30. P. Cironi, C. Cuevas, F. Albericio, and M. Álvarez, Tetrahedron, 2004, 60, 8669.
31. S. Ruchirawat and T. Mutarapat, Tetrahedron Lett., 2001, 42, 1205.
32. A. E. Tschitschibabin, Ber. 1927, 60, 1607;
33. C. Casagrande, A. Invernizzi, R. Ferrini, and G. Ferrari, J. Med. Chem., 1968, 11, 765.
34. Y. Tamaru, Y. Yamada, K. Inoue, Y. Yamamoto, and Z. Yoshida, J. Org. Chem., 1983, 48, 1286.
35. P. Ploypradith, W. Jinaglueng, C. Pavaro, and S. Ruchirawat, Tetrahedron Lett., 2003, 44, 1363.
36. P. Ploypradith, R. K. Kagan, and S. Ruchirawat, J. Org. Chem., 2005, 70, 5119.
37. P. Ploypradith, C. Mahidol, P. Sahakitpichan, S. Wongbundit, and S. Ruchirawat, Angew. Chem. Int. Ed., 2004, 43, 866.
38. C. A. Grob and K. Camenish, Helv. Chim. Acta, 1953, 36, 49.
39. P. Ploypradith, T. Petchmanee, P. Sahakitpichan, N. D. Litvinas, and S. Ruchirawat, J. Org. Chem., 2006, 71, 9440.
40. M. Chittchang, P. Batsomboon, S. Ruchirawat, and P. Ploypradith, ChemMedChem, 2009, 4, 457.
41. S. Boonya-udtayan, N. Yotapan, C. Woo, C. J. Bruns, S. Ruchirawat, and N. Thasana, Chem. Asian J., 2010, 5, 2113.
42. N. Thasana, R. Worayuthakarn, P. Kradanrat, E. Hohn, L. Young, and S. Ruchirawat, J. Org. Chem., 2007, 72, 9379.
43. P. Wipf and C. R. Hopkins, J. Org. Chem., 2001, 66, 3133.
44. B.-X. Zhao, Y. Yu, and S. Eguchi, Tetrahedron, 1996, 52, 12049.
45. M. Díaz, E. Guitián, and L. Castedo, Synlett, 2001, 1164.
46. S. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 1990, 55, 1736.
47. M. Nyerges and L. To'ke, Tetrahedron Lett., 2005, 46, 7531.
48. J. Tóth, A. Nedves, A. Dancsó, G. Blaskó, L. To'ke, and M. Nyerges, Synthesis, 2007, 1003.
49. J. S. Yadav, K. U. Gayathri, B. V. S. Reddy, and A. R. Prasad, Synlett, 2009, 43.
50. S. Hajra, B. Maji, and A. Karmakar, Tetrahedron Lett., 2005, 46, 8599.
51. J. C. Liermann and T. Opatz, J. Org. Chem., 2008, 73, 4526.
52. S. T. Handy, Y. Zhang, and H. Bregman, J. Org. Chem., 2004, 69, 2362.
53. V. Y. Kurotaev, V. Y. Sosnovskikh, I. B. Kutyashev, A. Y. Barkov, and Y. V. Shklyaev, Tetrahedron Lett., 2008, 49, 5376.
54. S. Su and J. A. Porco, Jr., J. Am. Chem. Soc., 2007, 129, 7744.
55. http://www.pharm.monash.edu.au/courses/honours/mipsprojects/mcda/bflynn3. html
56. For recent reviews on pyrrole synthesis, see: (a) M. G. Banwell, T. E. Goodwin, S. Ng, J. A. Smith, and D. J. Wong, Eur. J. Org. Chem., 2006, 3043;
57. F. Bellina and R. Rossi, Tetrahedron, 2006, 62, 7213;
58. C. Schmuck and D. Rupprecht, Synthesis, 2007, 3095.
59. A. Heim, A. Terpin, and W. Steglich, Angew. Chem., Int. Ed. Engl., 1997, 36, 155.
60. D. I. Davies and C. Waring, J. Chem. Soc., 1967, 1639.
61. P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, and F. Bilodeau, J. Am. Chem. Soc., 2006, 128, 11350;
62. L. J. Gooben, N. Rodríguez, and K. Gooben, Angew. Chem. Int. Ed., 2008, 47, 3100.
63. C. Peschko, C. Winklhofer, and W. Steglich, Chem. Eur. J., 2000, 6, 1147.
64. O. Hinsberg, Ber., 1910, 43, 901;
65. A. Merz, R. Schropp, and E. Dötterl, Synthesis, 1995, 795.
66. T. Oh-E, N. Miyaura, and A. Suzuki, J. Org. Chem., 1993, 58, 2201.
67. M. Iwao, T. Takeuchi, N. Fujikawa, T. Fukuda, and F. Ishibashi, Tetrahedron Lett., 2003, 44, 4443.
68. N. Fujikawa, T. Ohta, T. Yamaguchi, T. Fukuda, F. Ishibashi, and M. Iwao, Tetrahedron, 2006, 62, 594.
69. T. Fukuda, Y. Hayashida, and M. Iwao, Heterocycles, 2009, 77, 1105.
70. T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, and Y. Kita, J. Org. Chem., 1998, 63, 7698.
71. A. G. Myers, D. Tanaka, and M. R. Mannion, J. Am. Chem. Soc., 2002, 124, 11250;
72. D. Tanaka, S. P. Romeril, and A. G. Myers, J. Am. Chem. Soc., 2005, 127, 10323;
73. C. Wang, I. Piel, and F. Glorius, J. Am. Chem. Soc., 2009, 131, 4194.
74. T. Yamaguchi, T. Fukuda, F. Ishibashi, and M. Iwao, Tetrahedron Lett., 2006, 47, 3755.
75. T. Fukuda, T. Ohta, S. Saeki, and M. Iwao, Heterocycles, 2010, 80, 841.
76. Y. Liu, I. F. Lien, S. Ruttgaizer, P. Dove, and S. D. Taylor, Org. Lett., 2004, 6, 209.
77. S. Hirao, Y. Sugiyama, M. Iwao, and F. Ishibashi, Biosci. Biotechnol. Biochem., 2009, 73, 1764;
78. S. Hirao, Y. Yoshinaga, M. Iwao, and F. Ishibashi, Tetrahedron Lett., 2010, 51, 533.
79. K. Warabi, S. Matsunaga, R. W. M. van Soest, and N. Fusetani, J. Org. Chem., 2003, 68, 2765.
80. G. Blotny, Tetrahedron, 2006, 62, 9507.
81. J. L. Namy, J. Souppe, and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765.
82. A. Fürstner, M. M. Domostoj, and B. Scheiper, J. Am. Chem. Soc., 2006, 128, 8087;
83. K. Okano, H. Fujiwara, T. Noji, T. Fukuyama, and H. Tokuyama, Angew. Chem. Int. Ed., 2010, 49, 5925.
84. D. L. Boger, C. W. Boyce, M. A. Labroli, C. A. Sehon, and Q. Jin, J. Am. Chem. Soc., 1999, 121, 54.
85. D. L. Boger, D. R. Soenen, C. W. Boyce, M. P. Hedrick, and Q. Jin, J. Org. Chem., 2000, 65, 2479.
86. H. Kang and W. Fenical, J. Org. Chem., 1997, 62, 3254.
87. P. E. Eaton, G. R. Carlson, and J. T. Lee, J. Org. Chem., 1973, 38, 4071.
88. J. T. Gupton, K. E. Krumpe, B. S. Burnham, T. M. Webb, J. S. Shuford, and J. A. Sikorski, Tetrahedron, 1999, 55, 14515.
89. J. T. Gupton, S. C. Clough, R. B. Miller, J. R. Lukens, C, A. Henry, R. P. F. Kanters, and J. A. Sikorski, Tetrahedron, 2003, 59, 207.
90. J. T. Gupton, B. C. Giglio, J. E. Eaton, E. A. Rieck, K. L. Smith, M. J. Keough, P. J. Barelli, L. T. Firich, J. E. Hempel, T. M. Smith, and R. P. F. Kanters, Tetrahedron, 2009, 65, 4283.
91. D. H. R. Barton, J. Kervagoret, and S. Z. Zard, Tetrahedron, 1990, 46, 7587.
92. J. M. Bullington, R. R. Wolff, and P. F. Jackson, J. Org. Chem., 2002, 67, 9439.
93. M. G. Banwell, B. L. Flynn, E. Hamel, and D. C. R. Hockless, Chem. Commun., 1997, 207.
94. B. L. Bray, P. H. Mathies, R. Naef, D. R. Solas, T. T. Tidwell, D. R. Artis, and J. M. Muchowski, J. Org. Chem., 1990, 55, 6317.
95. M. G. Banwell, B. L. Flynn, D. C. R. Hockless, R. W. Longmore, and D. Rae, Aust. J. Chem., 1998, 52, 755.
96. S. T. Handy, Y. Zhang, and H. Bregman, J. Org. Chem., 2004, 69, 2362.
97. S. T. Handy, H. Bregman, J. Lewis, X. Zhang, and Y. Zhang, Tetrahedron Lett., 2003, 44, 427.
98. D. Pla, A. Marchal, C. A. Olsen, F. Albericio, and M. Álvarez, J. Org. Chem., 2005, 70, 8231.
99. C. A. Olsen, N. Parera, F. Albericio, and M. Álvarez, Tetrahedron Lett., 2005, 46, 2041.
100. D. Pla, A. Marchal, C. A. Olsen, A. Francesch, C. Cuevas, F. Albericio, and M. Álvarez, J. Med. Chem., 2006, 49, 3257.
101. T. Ohta, T. Fukuda, F. Ishibashi, and M. Iwao, J. Org. Chem., 2009, 74, 8143.
102. C. Zonta, F. Fabris, and O. De Lucchi, Org. Lett., 2005, 7, 1003.
103. T. Fukuda, T. Ohta, E. Sudo, and M. Iwao, Org. Lett., 2010, 12, 2734.
104. For a review, see: D. Alberico, M. E. Scott, and M. Lautens, Chem. Rev., 2007, 107, 174.
105. W. Qiu, S. Chen, X. Sun, Y. Liu, and D. Zhu, Org. Lett., 2006, 8, 867.
106. C. P. Ridley, M. V. R. Reddy, G. Rocha, F. D. Bushman, and D. J. Faulkner, Bioorg. Med. Chem., 2002, 10, 3285.
107. C. Tardy, M. Facompré, W. Laine, B. Baldeyrou, D. García-Gravalos, A. Francesch, C. Mateo, A. Pastor, J. A. Jiménez, I. Manzanares, C. Cuevas, and C. Bailly, Bioorg. Med. Chem., 2004, 12, 1697.
108. M. Facompré, C. Tardy, C. Bal-Mahieu, P. Colson, C. Perez, I. Manzanares, C. Cuevas, and C. Bailly, Cancer Res., 2003, 63, 7392.
109. E. Marco, W. Laine, C. Tardy, A. Lansiaux, M. Iwao, F. Ishibashi, C. Bailly, and F. Gago, J. Med. Chem., 2005, 48, 3796.
110. D. Pla, A. Francesch, P. Calvo, C. Cuevas, R. Aligué, F. Albericio, and M. Álvarez, Bioconjugate Chem., 2009, 20, 1100.
111. D. Pla, M. Martí, J. Farrera-Sinfreu, D. Pulido, A. Francesch, P. Calvo, C. Cuevas, M. Royo, R. Aligué, F. Albericio, and M. Álvarez, Bioconjugate Chem., 2009, 20, 1112.
112. J. Kluza, M.-A. Gallego, A. Loyens, J.-C. Beauvillain, J.-M. F. Sousa-Faro, C. Cuevas, P. Marchetti, and C. Bailly, Cancer Res., 2006, 66, 3177.
113. M.-A. Gallego, C. Ballot, J. Kluza, N. Hajji, A. Martoriati, L. Castéra, C. Cuevas, P. Formstecher, B. Joseph, G. Kroemer, C. Bailly, and P. Marchetti, Oncogene, 2008, 27, 1981.
114. C. Ballot, J. Kluza, A. Martoriati, U. Nyman, P. Formstecher, B. Joseph, C. Bailly, and P. Marchetti, Mol. Cancer Ther., 2009, 8, 3307.
115. C. Ballot, J. Kluza, S. Lancel, A. Martoriati, S. M. Hassoun, L. Mortier, J.-C. Vienne, G. Briand, P. Formstecher, C. Bailly, R. Nevière, and P. Marchetti, Apoptosis, 2010, 15, 769.
116. D. Baunbæk, N. Trinkler, Y. Ferandin, O. Lozach, P. Ploypradith, S. Ruchirawat, F. Ishibashi, M. Iwao, and L. Meijer, Mar. Drugs, 2008, 6, 514.
117. T.-C. Chou, Y. Guan, D. R. Soenen, S. J. Danishefsky, and D. L. Boger, Cancer Chemother. Pharmacol., 2005, 56, 379.