The psymberin story - Biological properties and approaches towards total and analogue syntheses

Angewandte Chemie - International Edition

Volumn 52, Issue 42, 2013, Pages 10960-10985

  Bielitza, Max ^a   Pietruszka, Jörg ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

anticancer agent; biosynthesis; natural products; structure activity relationships; total synthesis

Indexed keywords

ANTI-CANCER AGENTS; BIOLOGICAL PROPERTIES; MARINE NATURAL PRODUCTS; NATURAL PRODUCTS; STRUCTURE ACTIVITY RELATIONSHIPS; STRUCTURE ELUCIDATION; STRUCTURE-ACTIVITY STUDIES; TOTAL SYNTHESIS;

BIOCHEMISTRY; KETONES;

BIOSYNTHESIS;

ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; COUMARIN DERIVATIVE; PSYMBERIN;

ANIMAL; ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; MARINE BIOLOGY; NATURAL PRODUCTS; STRUCTURE ACTIVITY RELATION; STRUCTURE-ACTIVITY RELATIONSHIPS; SYNTHESIS; TOTAL SYNTHESIS;

ANTICANCER AGENT; BIOSYNTHESIS; NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

ANIMALS; BIOLOGICAL PRODUCTS; COUMARINS; HUMANS; MARINE BIOLOGY; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84885465000     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301259     Document Type: Article

References (115)

1. Selected reviews on marine polyketides
2. J. Staunton, K. J. Weissman, Nat. Prod. Rep. 2001, 18, 380-416
3. W. H. Gerwick, B. S. Moore, Chem. Biol. 2012, 19, 85-98
4. D. A. Akey, J. J. Gehret, D. Khare, J. L. Smith, Nat. Prod. Rep. 2012, 29, 1038-1049, and references therein.
5. R. H. Cichewicz, F. A. Valeriote, P. Crews, Org. Lett. 2004, 6, 1951-1954.
6. F. Z. Netolitzky, Z. Angew. Entomol. 1919, 5, 252-257.
7. M. Pavan, G. Bo, Phys. Com. Oecol. 1953, 3, 307-312.
8. A. Quilico, C. Cardani, D. Chiringhelli, M. Pavan, Chim. Ind. 1961, 43, 1434-1436.
9. C. Cardani, D. Ghiringhelli, R. Mondelli, A. Quilico, Tetrahedron Lett. 1965, 6, 2537-2545
10. C. Cardani, D. Ghiringhelli, R. Monelli, A. Quilico, Gazz. Chim. Ital. 1966, 96, 3-38.
11. T. Matsumoto, S. Yanagiya, S. Maeno, S. Yasuda, Tetrahedron Lett. 1968, 9, 6297-6300.
12. A. Furusaki, T. Watanabe, T. Matsumoto, M. Yanagiya, Tetrahedron Lett. 1968, 9, 6301-6304.
13. J. H. Frank, K. Kanamitsu, J. Med. Entomol. 1987, 24, 155-191.
14. A. W. R. McCrae, S. A. Visser, Ann. Trop. Med. Parasitol. 1975, 69, 109-120.
15. R. K. Armstrong, J. L. Winfield, Am. J. Trop. Med. Hyg. 1969, 18, 147-150.
16. L. Penchenier, J. Mouchet, B. Cros, P. Legall, J. Y. Cosnefroy, P. Quezede, J. Chandenier, Bull. Soc. Path. Exot. 1994, 87, 45-48.
17. A. N. Williams, J. R. Army Med. Corps 1993, 139, 17-19.
18. S. N. R. Qadir, N. Raza, S. B. Rahman, Dermatol. Online J. 2006, 12, 9.
19. O. Zargari, A. Kimyai-Asadi, F. Fathalikhani, M. Panahi, Int. J. Dermatol. 2003, 42, 608-612.
20. S. A. Norton, C. Lyons, Lancet 2002, 359, 1950.
21. Exodus 7:14-12:30.
22. M. Soldati, A. Fioretti, M. Ghione, Experientia 1966, 22, 176-178.
23. R. A. Mosey, P. E. Floreancig, Nat. Prod. Rep. 2012, 29, 980-995
24. Z. J. Witczak, R. M. Rampulla, A. Bommareddy, Mini-Rev. Med. Chem. 2012, 12, 1520-1532
25. F. Wu, M. E. Green, P. Floreancig, Angew. Chem. 2011, 123, 1163-1166
26. Angew. Chem. Int. Ed. 2011, 50, 1131-1134 and references therein.
27. J. Piel, Proc. Natl. Acad. Sci. USA 2002, 99, 14002-14007
28. J. Piel, I. Höfer, D. Hui, J. Bacteriol. 2004, 186, 1280-1286.
29. G. R. Pettit, J.-P. Xu, J.-C. Chapuis, R. K. Pettit, L. P. Tackett, D. L. Doubek, J. N. A. Hooper, J. M. Schmidt, J. Med. Chem. 2004, 47, 1149-1152.
30. S. Kiren, L. Williams, Org. Lett. 2005, 7, 2905-2908.
31. C. Cardani, C. Fuganti, D. Ghiringhelli, P. Grasselli, M. Pavan, M. D. Valcurone, Tetrahedron Lett. 1973, 14, 2815-2818.
32. K. M. Fisch, C. Gurgui, N. Heycke, S. A. vana dera Sar, S. A. Anderson, V. L. Webb, S. Taudien, M. Platzer, B. K. Rubio, S. J. Robinson, P. Crews, J. Piel, Nat. Chem. Biol. 2009, 5, 494-501.
33. A. Schirmer, R. Gadkari, C. D. Reeves, F. Ibrahim, E. F. DeLong, C. R. Hutchinson, Appl. Environ. Microbiol. 2005, 71, 4840-4849.
34. S. Sudek, N. B. Lopanik, L. E. Waggoner, M. Hildebrand, C. Anderson, H. Liu, A. Patel, D. H. Sherman, M. G. Haygood, J. Nat. Prod. 2007, 70, 67-74.
35. M. S. Donia, B. J. Hathaway, S. Sudek, M. G. Haygood, M. J. Rosovitz, J. Ravel, E. W. Schmidt, Nat. Chem. Biol. 2006, 2, 729-735.
36. N. S. Burres, J. J. Clement, Cancer Res. 1989, 49, 2935-2940.
37. H. Ogawara, K. Higashi, K. Uchino, N. B. Perry, Chem. Pharm. Bull. 1991, 39, 2152-2154.
38. A. Richter, P. Kocienski, P. Raubo, D. Davies, Anti-Cancer Drug Des. 1997, 12, 217-227.
39. K. A. Hood, L. M. West, P. T. Northcote, M. V. Berridge, J. H. Miller, Apoptosis 2001, 6, 207-219.
40. K.-H. Lee, S. Nishimura, S. Matsunaga, N. Fusetani, S. Horinouchi, M. Yoshida, Cancer Sci. 2005, 96, 357-364.
41. S. Nishimura, S. Matsunaga, M. Yoshida, H. Hirota, S. Yokoyama, N. Fusetani, Bioorg. Med. Chem. 2005, 13, 449-454.
42. T. Chinen, Y. Nagumo, T. Watanabe, T. Imaizumi, M. Shibuya, T. Kataoka, N. Kanoh, Y. Iwabuchi, T. Usui, Toxicol. Lett. 2010, 199, 341-346.
43. S. Wan, F. Wu, J. C. Rech, M. E. Green, R. Balachandran, W. S. Horne, B. W. Day, P. E. Floreancig, J. Am. Chem. Soc. 2011, 133, 16668-16679.
44. C.-Y. Wu, Y. Feng, E. R. Cardenas, N. Williams, P. E. Floreancig, J. K. Dea Brabander, M. G. Roth, J. Am. Chem. Soc. 2012, 134, 18998-19003.
45. X. Huang, N. Shao, A. Palani, R. Aslanian, A. Buevich, Org. Lett. 2007, 9, 2597-2600.
46. G. R. Pettit, C. L. Herald, D. L. Doubek, D. L. Herald, J. Am. Chem. Soc. 1982, 104, 6846-6848.
47. M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785
48. Angew. Chem. Int. Ed. Engl. 1996, 35, 1672-1675.
49. T. Nonomura, M. Sasaki, N. Matsumori, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1786-1789
50. Angew. Chem. Int. Ed. Engl. 1996, 35, 1675-1678.
51. K. Lee, H. Kim, J. Hong, Eur. J. Org. Chem. 2012, 1025-1032.
52. T. L. B. Boivin, Tetrahedron 1987, 43, 3309-3362.
53. P. A. Clarke, S. Santos, Eur. J. Org. Chem. 2006, 2045-2053.
54. I. Larrosa, P. Romea, F. Urpí, Tetrahedron 2008, 64, 2683-2723.
55. X. Jiang, J. Garcia-Fortanet, J. K. Dea Brabander, J. Am. Chem. Soc. 2005, 127, 11254-11255.
56. J. C. Rech, P. E. Floreancig, Org. Lett. 2005, 7, 5175-5178.
57. N. Shangguan, S. Kiren, L. J. Williams, Org. Lett. 2007, 9, 1093-1096.
58. A. B. Smith a III, J. A. Jurica, S. P. Walsh, Org. Lett. 2008, 10, 5625-5628.
59. H. Lachance, O. Marion, D. G. Hall, Tetrahedron Lett. 2008, 49, 6061-6064.
60. K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185-3187
61. Angew. Chem. Int. Ed. 2002, 41, 3059-3061.
62. L. E. Brown, Y. R. Landaverry, J. R. Davies, K. A. Milinkevich, S. Ast, J. S. Carlson, A. G. Oliver, J. P. Konopelski, J. Org. Chem. 2009, 74, 5405-5410.
63. M. T. Crimmins, J. M. Stevens, G. M. Schaaf, Org. Lett. 2009, 11, 3990-3993.
64. T. Watanabe, T. Imaizumi, T. Chinen, Y. Nagumo, M. Shibuya, T. Usui, N. Kanoh, Y. Iwabuchi, Org. Lett. 2010, 12, 1040-1043.
65. S. R. Byeon, H. Park, H. Kim, J. Hong, Org. Lett. 2011, 13, 5816-5819.
66. W. J. Buffham, N. A. Swain, S. L. Kostiuk, T. P. Gonçalves, D. C. Harrowven, Eur. J. Org. Chem. 2012, 1217-1222.
67. M. Bielitza, J. Pietruszka, Synlett 2012, 1625-1628.
68. Y. Feng, X. Jiang, J. K. Dea Brabander, J. Am. Chem. Soc. 2012, 134, 17083-17093.
69. M. Bielitza, J. Pietruszka, Chem. Eur. J. 2013, 19, 8300-8308.
70. R. D. Barry, Chem. Rev. 1964, 64, 229-260.
71. N. Choukchou-Braham, Y. Asakawa, J.-P. Lepoittevin, Tetrahedron Lett. 1994, 35, 3949-3952.
72. J. J. Fitzgerald, A. R. Pagano, V. M. Sakoda, R. A. Olofson, J. Org. Chem. 1994, 59, 4117-4121.
73. A. Ramacciotti, R. Fiaschi, E. Napolitano, J. Org. Chem. 1996, 61, 5371-5374.
74. P. Salvadori, S. Superchi, F. Minutolo, J. Org. Chem. 1996, 61, 4190-4191.
75. S. Superchi, F. Minutolo, D. Pini, P. Salvadori, J. Org. Chem. 1996, 61, 3183-3186.
76. K. Uchida, H. Watanabe, T. Kitahara, Tetrahedron 1998, 54, 8975-8984.
77. Y. Kurosaki, T. Fukuda, M. Iwao, Tetrahedron 2005, 61, 3289-3303.
78. T. Suzuki, T. Yamada, K. Watanabe, T. Katoh, Bioorg. Med. Chem. Lett. 2005, 15, 2583-2585.
79. S. K. Mandal, S. C. Roy, Tetrahedron Lett. 2007, 48, 4131-4134.
80. A. Habel, W. Boland, Org. Biomol. Chem. 2008, 6, 1601-1604.
81. S. K. Mandal, S. C. Roy, Tetrahedron 2008, 64, 11050-11057.
82. M. Sher, A. Ali, H. Reinke, P. Langer, Tetrahedron Lett. 2008, 49, 5400-5402.
83. M. D. Obushak, V. S. Matiychuk, V. V. Turytsya, Tetrahedron Lett. 2009, 50, 6112-6115.
84. A. Rioz-Martínez, G. dea Gonzalo, D. E. T. Pazmiño, M. W. Fraaije, V. Gotor, J. Org. Chem. 2010, 75, 2073-2076.
85. S. Pal, V. Chatare, M. Pal, Curr. Org. Chem. 2011, 15, 782-800.
86. J. Chen, L. Zhou, C. K. Tan, Y.-Y. Yeung, J. Org. Chem. 2012, 77, 999-1009.
87. D. Hojo, K. Noguchi, M. Hirano, K. Tanaka, Angew. Chem. 2008, 120, 5904-5906
88. Angew. Chem. Int. Ed. 2008, 47, 5820-5822.
89. M. F. Hentemann, J. G. Allen, S. J. Danishefsky, Angew. Chem. 2000, 112, 2013-2016
90. Angew. Chem. Int. Ed. 2000, 39, 1937-1940.
91. P. Langer, B. Kracke, Tetrahedron Lett. 2000, 41, 4545-4547.
92. M. E. Green, J. C. Rech, P. E. Floreancig, Org. Lett. 2005, 7, 4117-4120.
93. B. Henßen, E. Kasparyan, G. Marten, J. Pietruszka, Heterocycles 2007, 245-249.
94. S. V. Ley, E. Diez, D. J. Dixon, R. T. Guy, P. Michel, G. L. Nattrass, T. D. Sheppard, Org. Biomol. Chem. 2004, 2, 3608-3617.
95. S. V. Ley, D. J. Dixon, R. T. Guy, M. A. Palomero, A. Polara, F. Rodriguez, T. D. Sheppard, Org. Biomol. Chem. 2004, 2, 3618-3627.
96. J. Pietruszka, R. C. Simon, Eur. J. Org. Chem. 2009, 3628-3634.
97. A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752-1755.
98. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204-2206
99. Angew. Chem. Int. Ed. 2004, 43, 2152-2154.
100. D. A. Evans, M. A. Calter, Tetrahedron Lett. 1993, 34, 6871-6874.
101. X. Huang, N. Shao, A. Palani, R. Aslanian, A. Buevich, C. Seidel-Dugan, R. Huryk, Tetrahedron Lett. 2008, 49, 3592-3595.
102. S. Wan, M. E. Green, J.-H. Park, P. E. Floreancig, Org. Lett. 2007, 9, 5385-5388.
103. Q. Xiao, P. E. Floreancig, Org. Lett. 2008, 10, 1139-1142.
104. M. V. DeBenedetto, M. E. Green, S. Wan, J.-H. Park, P. E. Floreancig, Org. Lett. 2009, 11, 835-838.
105. C. Lu, Q. Xiao, P. E. Floreancig, Org. Lett. 2010, 12, 5112-5115.
106. G. Erker, W. Frömberg, J. L. Atwood, W. E. Hunter, Angew. Chem. 1984, 96, 72-73
107. Angew. Chem. Int. Ed. Engl. 1984, 23, 68-69.
108. A. Maraval, A. Igau, B. Donnadieu, J.-P. Majoral, Eur. J. Org. Chem. 2003, 385-394.
109. C. An, A. T. Hoye, A. B. Smith, Org. Lett. 2012, 14, 4350-4353; after acceptance of the present Review a Full Paper was published
110. C. An, J. A. Jurica, S. P. Walsh, A. T. Hoye, A. B. Smith, J. Org. Chem. 2013, 78, 4278-4296.
111. X. Jiang, N. Williams, J. K. Dea Brabander, Org. Lett. 2007, 9, 227-230.
112. X. Huang, N. Shao, R. Huryk, A. Palani, R. Aslanian, C. Seidel-Dugan, Org. Lett. 2009, 11, 867-870
113. N. Shao, X. Huang, A. Palani, R. Aslanian, J. Piwinski, R. Huryk, C. Seidel-Dugan, Synthesis 2009, 2855-2872.
114. G. R. Pettit, Z. A. Chicacz, F. Gao, C. L. Herald, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, J. Org. Chem. 1993, 58, 1302-1304.
115. S. Osman, B. J. Albert, Y. Wang, M. Li, N. L. Czaicki, K. Koide, Chem. Eur. J. 2011, 17, 895-904.