Marine toxins with spiroimine rings: Total synthesis of pinnatoxin A

European Journal of Organic Chemistry

Volumn , Issue 30, 2010, Pages 5743-5765

  Beaumont, Stéphane ^a   Ilardi, Elizabeth A ^a   Tappin, Nicholas D C ^a   Zakarian, Armen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Marine toxins; Natural products; Pinnatoxin; Spiro compounds; Spiroimine natural products; Total synthesis

Indexed keywords

EID: 78249262123     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000842     Document Type: Article

References (77)

1. For a relevant overview of these compounds:, J. Molgó, E. Girard, E. Benoit, in: Phycotoxins: Chemistry and Biochemistry (Eds.:, L. M. Botana,), Blackwell Publishing, 2007, pp. 319-355.
2. M. Kita, D. Uemura, Chem. Lett. 2005, 34, 454 - 459.
3. M. Kuramoto, H. Arimoto, D. Uemura, Mar. Drugs 2004, 2, 39 - 54.
4. T. Chou, T. Haino, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1996, 37, 4027 - 4030.
5. B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621 - 2624.
6. S. Z. Zheng, F. L. Huang, S. C. Chen, X. F. Tan, J. B. Zhuo, J. Peng, R. W. Xie, Chin. J. Mar. Drugs. 1990, 33, 33 - 35.
7. J. Rosewater, Indo-Pacific Mollusca 1961, 1, 175 - 226.
8. D. Uemura, T. Chuo, T. Haino, A. Nagatsu, S. Fukuzawa, S. Zheng, H. Chen, J. Am. Chem. Soc. 1995, 117, 1155 - 1156.
9. M. Kita, D. Uemura, Prog. Mol. Subcellular Biol. 2006, 43, 25 - 51.
10. For a review concerning toxicologies:, R. Munday, in: Seafood and Freshwater Toxins: Pharmacology, Physiology and Detection, 2nd ed. (Ed.:, L. M. Botana,), CRC Press, 2008, pp. 581-594.
11. N. Takada, N. Umemura, K. Suenaga, T. Chou, A. Nagatsu, T. Haino, K. Yamada, D. Uemura, Tetrahedron Lett. 2001, 42, 3491 - 3494.
12. D. R. Tindall, R. W. Dickey, R. D. Carlson, G. Morey-Gaines, ACS Symposium, Series 262, American Chemical Society, Washington DC, 1984, pp. 225-240.
13. Selected examples
14. D. F. Martin, G. M Padilla, in: Bioactive Compounds from the Sea Martin, vol. 1 (Eds.:, H. J. Humm, C. E. Lane,), Marcel Dekker Inc. New York, 1974, pp. 151-174.
15. Y. Y. Lin, M. Risk, S. M. Ray, D. Van Engen, J. Clardy, J. Golik, J. C. James, K. Nakanishi, J. Am. Chem. Soc. 1981, 103, 6773 - 6775.
16. for a review on polyketide compounds from dinoflagellate sources, see:, K. S. Rein, J. Borrone, J. Compl. Biochem. Phys. Part B 1999, 124, 117.
17. D. M. Anderson, in: Physiological Ecology of Harmful Algal Blooms (Eds.:, D. M. Anderson, A. D. Cembella, G. M. Hallegraeff,), Springer, 1998, pp. 29-48.
18. Bivalve Molluscs as Vectors of Marine Biotoxins Involved in Seafood Poisoning, P. Ciminiello, E. Fattorusso, Prog. Mol. Subcellular Biol. 2006, 43, 52 - 82.
19. A. D. Cembella, N. I. Lewis, M. A. Quilliam, Phycologia 2000, 39, 67 - 74.
20. T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. M. Watson-Wright, J. L. C. Wright, J. Chem. Soc., Chem. Commun. 1995, 2159 - 2161.
21. M. Falk, I. W. Burton, T. Hu, J. A. Walter, J. L. C. Wright, Tetrahedron 2001, 57, 8659 - 8665.
22. T. Hu, J. M. Curtis, J. A. Walter, J. L. C. Wright, Tetrahedron Lett. 1996, 37, 7671 - 7674.
23. T. Seki, M. Satake, L. Mackenzie, H. F. Kaspar, T. Yasumoto, Tetrahedron Lett. 1995, 36, 7093 - 7096.
24. M. Stewart, J. W. Blunt, M. H. G. Munro, W. T. Robinson, D. T. Hannah, Tetrahedron Lett. 1997, 38, 4889 - 4890.
25. R. Munday, N. R. Towers, L. Mackenzie, V. Beuzenberg, P. T. Holland, C. O. Miles, Toxicon 2004, 44, 173 - 178.
26. Gymnodimine B:, C. O. Miles, A. L. Wilkins, D. J. Stirling, A. L. MacKenzie, J. Agric. Food Chem. 2000, 48, 1373 - 1376.
27. gymnodimine C:, C. O. Miles, A. L. Wilkins, D. J. Stirling, A. L. MacKenzie, J. Agric. Food Chem. 2003, 51, 4838 - 4840. For a recent total synthesis of (-)-gymnodimine, see
28. K. Kong, D. Romo, C. Lee, Angew. Chem. Int. Ed. 2009, 48, 7402-7405 and studies
29. Y. Ahn, G. I. Cardenas, J. Yang, D. Romo, Org. Lett. 2001, 3, 751 - 754.
30. C. Lu, G. Lee, R. Huang, H. Chou, Tetrahedron Lett. 2001, 42, 1713 - 1716.
31. K. Torigoe, M. Murata, T. Yasumoto, J. Am. Chem. Soc. 1988, 110, 7876 - 7877.
32. T. Hu, A. S. W. de Freitas, J. M. Curtis, Y. Oshima, J. A. Walter, J. L. C. Wright, J. Nat. Prod. 1996, 59, 1010 - 1014.
33. K. Tachibana, F. J. Scheuer, J. Am. Chem. Soc. 1981, 103, 3469 - 2471.
34. A. D. Cembella, J. Appl. Phycology 1 1989, 307 - 310.
35. N. Takada, N. Uemura, K. Suenaga, D. Uemura, Tetrahedron Lett. 2001, 42, 3495 - 3497.
36. F. Matsuura, R. Peters, M. Anada, S. S. Harried, J. Hao, Y. Kishi, J. Am. Chem. Soc. 2006, 128, 7463 - 7465.
37. J. Hao, F. Matsuura, Y. Kishi, M. Kita, D. Uemura, N. Asai, T. Iwashita, J. Am. Chem. Soc. 2006, 128, 7742 - 7743.
38. For a review on bis-spiroketal systems, see:, M. A. Brimble, D. P. Furkert, Curr. Org. Chem. 2003, 7, 1461 - 1484.
39. S. L. MacKinnon, A. D. Cembella, I. W. Burton, N. Lewis, P. LeBlanc, J. A. Walter, J. Org. Chem. 2006, 71, 8724 - 8731.
40. F. Matsuura, J. Hao, R. Reents, Y. Kishi, Org. Lett. 2006, 8, 3327 - 3330.
41. J. A. McCauley, K. Nagasawa, P. A. Lander, S. G. Mischke, M. A. Semones, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 7647 - 7648.
42. For the BCDEF-ring fragment, see
43. T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379 - 7382.
44. T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541 - 544.
45. J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392 - 1393. For the A-ring fragment, see
46. J. Ishihara, M. Horie, Y. Shimada, S. Tojo, A. Murai, Synlett 2002, 3, 403 - 406. 1,7,9-Trioxadispiro[5.1.5.2]pentadecane structural studies
47. J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603 - 606.
48. P. Sinaÿ, J. R. Pougny, Tetrahedron Lett. 1976, 17, 4073 - 4076.
49. R. R. Schmidt, J. Michel, Carbohydr. Chem. 1985, 4, 141 - 169.
50. R. U. Lemieux, R. M. Ratcliffe, Can. J. Chem. 1979, 57, 1244 - 1251.
51. S. Sakamoto, H. Sakazaki, K. Hagiwara, K. Kamada, K. Ishii, T. Noda, M. Inoue, M. Hirama, Angew. Chem. Int. Ed. 2004, 43, 6505 - 6510.
52. T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett 1998, 298 - 300.
53. P. L. Barili, G. Berti, G. Catelani, C. Cini, F. D'Andrea, E. Mastrorilli, Carbohydr. Res. 1995, 278, 43 - 57.
54. 2 for the intramolecular alkylation starting from a diastereomeric mixture; refer to:, A. Nitta, A. Ishiwata, T. Noda, M. Hirama, Synlett 1999, 695, and references cited therein.
55. S. Nakamura, F. Kikuchi, S. Hashimoto, Angew. Chem. 2008, 120, 7199 - 7202.
56. S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353 - 10374.
57. S. Nakamura, S. Kikuchi, S. Hashimoto, Tetrahedron: Asymmetry 2008, 19, 1059 - 1067.
58. C. E. Stivala, A. Zakarian, J. Am. Chem. Soc. 2008, 130, 3774.
59. M. Pelc, A. Zakarian, Org. Lett. 2005, 7, 1629 - 1631.
60. M. Pelc, A. Zakarian, Tetrahedron Lett. 2006, 47, 7519 - 7523.
61. Unpublished studies by M. Pelc, Florida State University, 2005.
62. Y. Qin, C. E. Stivala, A. Zakarian, Angew. Chem. 2007, 46, 7466.
63. C. E. Stivala, A. Zakarian, Tetrahedron Lett. 2007, 48, 6845 - 6848.
64. C. E. Stivala, A. Zakarian, Org. Lett. 2009, 11, 839 - 842.
65. R. E. Ireland, R. H. Mueller, A. K. Willard, J. Am. Chem. Soc. 1976, 98, 2888.
66. X. Sun, D. B. Collum, J. Am. Chem. Soc. 2000, 122, 2452.
67. F. E. Romesberg, D. B. Collum, J. Am. Chem. Soc. 1995, 117, 2166.
68. F. E. Romesberg, D. B. Collum, J. Am. Chem. Soc. 1995, 117, 2166.
69. C. M. Cain, R. P. C. Cousins, G. Coumbarides, N. S. Simpkins, Tetrahedron 1990, 46, 523.
70. R. Shirai, M. Tanaka, K. Koga, J. Am. Chem. Soc. 1986, 108, 543.
71. R. Shirai, K. Aoki, D. Sato, H.-D. Kim, M. Murakata, T. Yasakuta, K. Koga, Chem. Pharm. Bull. 1994, 42, 690.
72. R. Shirai, K. Aoki, D. Sato, M. Tanaka, H. Kawasaki, K. Koga, Tetrahedron 1997, 53, 5963.
73. C. D. Lu, A. Zakarian, Org. Lett. 2007, 9, 3161 - 3163.
74. C. D. Lu, A. Zakarian, Org. Synth. 2008, 85, 158 - 171.
75. For application of this process in the synthesis of other natural products, see:, E. A. Ilardi, M. J. Isaacman, Y. Qin, S. A. Shelly, A. Zakarian, Tetrahedron 2009, 65, 3261 - 3269.
76. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry; Pergamon Press, Oxford, 1983.
77. E. Juaristi, G. Cuevas, The Anomeric Effect, CRC Press, Boca Raton, 1995.