SmI2-induced cyclizations and their applications in natural product synthesis

Chemical Record

Volumn 10, Issue 3, 2010, Pages 159-172

  Tadashi, Nakata ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Brevetoxin b; Oxepanes; Polycyclic ethers; Tetrahydropyrans; Total synthesis

Indexed keywords

BIOLOGICAL PRODUCT; BREVENAL (POLYETHER); BREVETOXIN B; CIGUATOXIN; ETHER DERIVATIVE; FUSED HETEROCYCLIC RINGS; GAMBIEROL; HEMIBREVETOXIN B; IODIDE; LACTONE; MAITOTOXIN; MARINE TOXIN; MUCOCIN; OXOCIN DERIVATIVE; POLYMER; PYRAN DERIVATIVE; SAMARIUM; SAMARIUM DIIODIDE;

CHEMISTRY; CYCLIZATION; REVIEW; SYNTHESIS;

BIOLOGICAL PRODUCTS; CIGUATOXINS; CYCLIZATION; ETHERS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; IODIDES; LACTONES; MARINE TOXINS; OXOCINS; POLYMERS; PYRANS; SAMARIUM;

EID: 77953664284     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.200900027     Document Type: Article

References (98)

1. Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
2. For reviews on polycyclic ethers, see: Yasumoto T.; Murata, M. Chem. Rev. 1993, 93, 1897
3. Shimizu, Y. Chem. Rev. 1993, 93, 1685
4. Murata M.; Yasumoto, T. Nat. Prod. Rep. 2000, 17, 293
5. Yasumoto, T. Chem. Rec. 2001, 1, 228
6. Deranas, A. H.; Norte M.; Fernández, J. J. Toxicon 2001, 39, 1101.
7. For reviews on synthetic methods and total syntheses, see: Alvarez, E.; Candenas, M-L.; Pérez, R.; Ravelo W.; Martín, J. D. Chem. Rev. 1995, 95, 1953
8. Fujiwara, K.; Hayashi, N.; Tokiwano T.; Murai, A. Heterocycles 1999, 50, 561
9. Mori, Y. Chem. Eur. J. 1997, 3, 849
10. Marmsäter F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4346
11. Inoue, M. Org. Biomol. Chem. 2004, 2, 1811
12. Fujiwara K.; Murai, A. Bull. Chem. Soc. Jpn. 2004, 77, 2129
13. Sasaki M.; Fuwa, H. Synlett, 2004, 1851
14. Kadota I.; Yamamoto, Y. Acc. Chem. Res. 2005, 38, 423
15. Nakata, T. Chem. Rev. 2005, 105, 4314
16. Inoue, M. Chem. Rev. 2005, 105, 4379
17. Clark, J. S. Chem. Commun. 2006, 3571
18. Sasaki, M. Bull. Chem. Soc. Jpn. 2007, 80, 856
19. Fuwa, H.; Sasaki, M Curr. Opin. Drug Disc. Dev. 2007, 10, 784
20. Sasaki, M.; Huwa, H. Nat. Prod. Rep. 2008, 25, 401
21. Nicolaou, K. C.; Frederick, M. O.; Aversa, R. J. Angew. Chem. Int. Ed. 2008, 47, 7182.
22. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935
23. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558.
24. Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Tiebes, J.; Xiao, X. -Y.; Hwang, C. -K.; Duggan, M. E.; Yang, Z.; Couladouros, E. A.; Sato, F.; Shin, J.; He, H. -M.; Bleckman, T. J. Am. Chem. Soc. 1995, 117, 10239
25. Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252.
26. Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios K. A.; Gartner, P. Nature 1998, 392, 264.
27. Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri H.; Satake, M. Science 2001, 294, 1904
28. Inoue, M.; Uehara, H.; Maruyama M.; Hirama, M. Org. Lett. 2002, 4, 4551
29. Inoue, M.; Miyazaki, K.; Uehara, H.; Maruyama M.; Hirama, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12013
30. Inoue M. Hirama, M. Acc. Chem. Res. 2004, 37, 961.
31. Inoue, M.; Miyazaki, K.; Ishihara, Y.; Tamami, A.; Ohnuma, Y.; Kawada, Y.; Komano, K.; Yamashita, S.; Lee N.; Hirama, M. J. Am. Chem. Soc. 2006, 128, 9352.
32. Fuwa, H.; Sasaki, M.; Satake M.; Tachibana, K. Org. Lett. 2002, 4, 2981
33. Fuwa, H.; Kainuma, N.; Tachibana K.; Sasaki, M. J. Am. Chem. Soc. 2002, 124, 14983.
34. Kadota, I.; Takakuma, H.; Sato, K.; Ohno, A.; Matsuda K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46
35. Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Satake M.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893.
36. Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc. 2005, 127, 848.
37. Furuta, H.; Hasegawa Y.; Mori, Y. Org. Lett. 2009, 11, 4382.
38. Tsukano C.; Sasaki, M. J. Am. Chem. Soc. 2003, 125, 14294
39. Tsukano, C.; Ebine M.; Sasaki, M. J. Am. Chem. Soc. 2005, 127, 4326.
40. Matsuo, G.; Kawamura, K.; Hori, N.; Matsukura, H.; Nakata, T. J. Am. Chem. Soc. 2004, 126, 14374.
41. Kadota, I.; Takamura, H.; Nishii H.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9246.
42. Fuwa, H.; Ebine, M.; Bourdelais, A. J.; Baden D. G.; Sasaki, M. J. Am. Chem. Soc. 2006, 128, 16989.
43. Takamura, H.; Kikuchi, S.; Nakamura, Y.; Yamagami, Y.; Kishi, T.; Kadota, I.; Yamamoto, Y. Org. Lett. 2009, 11, 2531.
44. Crimmins, M. T.; Zuccarello, J. L.; Ellis, J. M.; McDougall, P. J.; Haile, P. A.; Parrish, J. D.; Emmitte, K. A. Org. Lett. 2009, 11, 489
45. Crimmins, M. T.; Ellis, J. M.; Emmitte, K. A.; Haile, P. A.; McDougall, P. J.; Parrish, J. D.; Zuccarello, J. L. Chem. Eur. J. 2009, 15, 9223
46. Crimmins, M. T.; Zuccarello, J. L.; McDougall, P. J.; Ellis, J. M. Chem. Eur. J. 2009, 15, 9235.
47. Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811
48. Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron 2002, 58, 1853.
49. Nakata, T. J. Syn. Org. Chem. Jpn. 2008, 66, 344.
50. For reviews, see: Kagan, H. B. New J. Chem. 1990, 14, 453
51. Molander, G. A. Chem. Rev. 1992, 92, 29
52. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
53. Cf. Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C.; Yun, M.; Kim, S. Tetrahedron Lett. 1994, 35, 129.
54. Hori, N.; Matsukura, H.; Nakata, T. Org. Lett. 1999, 1, 1099.
55. Matsuo, G.; Kadohama, H.; Nakata, T. Chem. Lett. 2002, 148.
56. Matsuo, G.; Hori, N.; Nakata, T. Tetrahedron Lett. 1999, 40, 8859.
57. Sakamoto, Y.; Matsuo, G.; Matsukura, H.; Nakata, T. Org. Lett. 2001, 3, 2749.
58. Suzuki, K.; Matsukura, H.; Matsuo, G.; Koshino, H.; Nakata, T. Tetrahedron Lett. 2002, 43, 8653.
59. Kimishima, A.; Nakata, T. Tetrahedron Lett. 2008, 49, 6563.
60. Maemoto, M.; Kimishima, A.; Nakata, T. Org. Lett. 2009, 11, 4814.
61. The same type of reaction using tetrahydrofuran derivatives was reported. Donohoe, T. J.; Williams, O.; Churchill, G. H. Angew. Chem. Int. Ed. 2008, 47, 2869.
62. Kimura, T.; Nakata, T. Tetrahedron Lett. 2007, 48, 43.
63. Kimura, T.; Miyagawa, Y.; Ozawa, S.; Hagiwara, M.; Nakata, T. Heterocycles 2009, 77, 829.
64. Kimura, T.; Hagiwara, M.; Nakata, T. Tetrahedron Lett. 2007, 48, 9171
65. Kimura, T.; Hagiwara, M.; Nakata, T. Tetrahedron 2009, 65, 10893.
66. Jung, J. H.; Kim, Y. W.; Kim, M. A.; Choi, S. Y.; Chung, Y. K.; Kim, T.-R.; Shin, S.; Lee, E. Org. Lett. 2007, 9, 3225.
67. Nicolaou, K. C.; Prasad, C. V. C.; Hwang, C.-K.; Duggan, M. E.; Veale, C. A. J. Am. Chem. Soc. 1989, 111, 5321
68. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330
69. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang C.-K. Tetrahedron 1990, 46, 4517.
70. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361
71. Morohashi, A.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1999, 40, 97.
72. Saito, T.; Nakata, T. Org. Lett. 2009, 11, 113.
73. Saito, T.; Nakata, T. 50th Symposium on the Chemistry of Natural Products; Fukuoka, Japan, October 2008; Symposium papers, pp. 233-238.
74. Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060
75. Murata, M.; Naoki, H.; Matsunaga, S.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1994, 116, 7098
76. Satake, M.; Ishida, S.; Yasumoto, T.; Murata, M.; Utsumi, H.; Hinomoto, T. J. Am. Chem. Soc. 1995, 117, 7019.
77. Zheng, W.; DeMattei, J. A.; Wu, J.-P.; Duan, J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946.
78. Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1672
79. Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1675.
80. Morita, M.; Ishiyama, S.; Koshino, H.; Nakata, T. Org. Lett. 2008, 10, 1675.
81. Morita, M.; Haketa, T.; Koshino, H.; Nakata, T. Org. Lett. 2008, 10, 1679.
82. Satoh, M.; Koshino, H.; Nakata, T. Org. Lett. 2008, 10, 1683.
83. Nagatomo, M; Nakata, T. Heterocycles 2008, 76, 1069.
84. Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z -M.; Zhao, G-x.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409.
85. Takahashi, S.; Kubota, A.; Nakata, T. Angew. Chem. Int. Ed. 2002, 41, 4751.
86. Takahashi, S.; Kubota, A.; Nakata, T. Org. Lett. 2003, 5, 1353.
87. Takahashi, S.; Ogawa, N.; Koshino, H.; Nakata, T. Org. Lett. 2005, 7, 2783.
88. Bourdelais, A. J.; Campbell, S.; Jacocks, H.; Naar, J.; Wright, J. L. C.; Carsi, J.; Baden, D. G. Cell. Mol. Neurobiol. 2004, 24, 553
89. Bourdelais, A. J.; Jacocks, H. M.; Wright, J. L. C.; Bigwarfe, P. M., Jr.; Baden, D. G. J. Nat. Prod. 2005, 68, 2.
90. Su, J.-H.; Huang, H.-C.; Chao, C.-H.; Yan, L.-Y.; Wu, Y.-C.; Wu, C.-C.; Sheu, J.-H. Bull. Chem. Soc. Jpn. 2005, 78, 877.
91. Clark, J. S.; Hayes, S. T.; Wilson, C.; Gobbi, L. Angew. Chem. Int. Ed. 2007, 46, 437.
92. Satake, M.; Bourdelais, A. J.; Van Wagoner, R. M.; Baden, D. G.; Wright, J. L. Org. Lett. 2008, 10, 3465.
93. Kuranaga, T.; Shirai, T.; Baden, D. G.; Wright, J. L. C.; Satake, M.; Tachibana, K. Org. Lett. 2009, 11, 217
94. Fadeyi, O. O.; Lindsley, C. W. Org. Lett. 2009, 11, 3950
95. Ghosh, A. K.; Li, J. Org. Lett. 2009, 11, 4164
96. Lee, J.; Panek, J. S. Org. Lett. 2009, 11, 4389.
97. Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett. 1996, 37, 217
98. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.