SCOPUS 정보 검색 플랫폼 - 논문 보기

메뉴 건너뛰기

Volumn 67, Issue 35, 2011, Pages 6616-6626

Stereoselective synthesis of the left wing of Caribbean ciguatoxin

(3) Yamashita, Shuji a Uematsu, Ryohei a Hirama, Masahiro a

a TOHOKU UNIVERSITY (Japan)

Author keywords

Caribbean ciguatoxin; Convergent synthesis; Polycyclic ether; Radical cyclization

Indexed keywords

CIGUATOXIN;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; RADICAL CYCLIZATION; STEREOCHEMISTRY; TOXIN STRUCTURE; TOXIN SYNTHESIS;

CIGUATERA;

EID: 79960962442 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2011.05.080 Document Type: Article

Times cited : (14)

References (67)

1
- 0035239230
- R.J. Lewis Toxicon 39 2001 97 106
- (2001) Toxicon , vol.39 , pp. 97-106
- Lewis, R.J.¹

2
- 1542502091
- T. Yasumoto, and M. Murata Chem. Rev. 93 1993 1897 1909
- (1993) Chem. Rev. , vol.93 , pp. 1897-1909
- Yasumoto, T.¹ Murata, M.²

3
- 0028008326
- P.J. Scheuer Tetrahedron 50 1994 3 18
- (1994) Tetrahedron , vol.50 , pp. 3-18
- Scheuer, P.J.¹

4
- 0001476334
- T. Yasumoto, I. Nakajima, R. Bagnis, and R. Adachi Bull. Jpn. Soc. Sci. Fish. 43 1977 1015 1026
- (1977) Bull. Jpn. Soc. Sci. Fish. , vol.43 , pp. 1015-1026
- Yasumoto, T.¹ Nakajima, I.² Bagnis, R.³ Adachi, R.⁴

5
- 0024815125
- M. Murata, A.-M. Legrand, Y. Ishibashi, and T. Yasumoto J. Am. Chem. Soc. 111 1989 8929 8931
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8929-8931
- Murata, M.¹ Legrand, A.-M.² Ishibashi, Y.³ Yasumoto, T.⁴

6
- 0025045174
- M. Murata, A.-M. Legrand, Y. Ishibashi, M. Fukui, and T. Yasumoto J. Am. Chem. Soc. 112 1990 4380 4386
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 4380-4386
- Murata, M.¹ Legrand, A.-M.² Ishibashi, Y.³ Fukui, M.⁴ Yasumoto, T.⁵

7
- 0029263484
- T. Yasumoto, M. Fukui, K. Sasaki, and K. Sugiyama J. AOAC Int. 78 1995 574 582
- (1995) J. AOAC Int. , vol.78 , pp. 574-582
- Yasumoto, T.¹ Fukui, M.² Sasaki, K.³ Sugiyama, K.⁴

8
- 77955842414
- For recent researches on ciguatera and marine toxins, see: special issue on 'Ciguatera and Related Biotoxins,' Toxicon 56 2010 653 847 and references cited therein
- (2010) Toxicon , vol.56 , pp. 653-847

9
- 0031781515
- R.J. Lewis, J.-P. Vernoux, and I.M. Brereton J. Am. Chem. Soc. 120 1998 5914 5920
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5914-5920
- Lewis, R.J.¹ Vernoux, J.-P.² Brereton, I.M.³

10
- 77954627485
- P. Otero, S. Pérez, A. Alfonso, C. Vale, P. Rodríguez, N.N. Gouveia, N. Gouveia, J. Delgado, P. Vale, M. Hirama, Y. Ishihara, J. Molgó, and L.M. Botana Anal. Chem. 82 2010 6032 6039
- (2010) Anal. Chem. , vol.82 , pp. 6032-6039
- Otero, P.¹ Pérez, S.² Alfonso, A.³ Vale, C.⁴ Rodríguez, P.⁵ Gouveia, N.N.⁶ Gouveia, N.⁷ Delgado, J.⁸ Vale, P.⁹ Hirama, M.¹⁰ Ishihara, Y.¹¹ Molgó, J.¹² Botana, L.M.¹³

11
- 79960959464
- submitted for publication
- Yogi, K.; Oshiro, N.; Inafuku, Y.; Hirama, M.; Yasumoto, T., submitted for publication.
- Yogi, K.¹ Oshiro, N.² Inafuku, Y.³ Hirama, M.⁴ Yasumoto, T.⁵

12
- 0034709383
- T. Yasumoto, T. Igarashi, A.-M. Legrand, P. Cruchet, M. Chinain, T. Fujita, and H. Naoki J. Am. Chem. Soc. 122 2000 4988 4989
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4988-4989
- Yasumoto, T.¹ Igarashi, T.² Legrand, A.-M.³ Cruchet, P.⁴ Chinain, M.⁵ Fujita, T.⁶ Naoki, H.⁷

13
- 0027520944
- M. Satake, M. Murata, and T. Yasumoto Tetrahedron Lett. 34 1993 1975 1978
- (1993) Tetrahedron Lett. , vol.34 , pp. 1975-1978
- Satake, M.¹ Murata, M.² Yasumoto, T.³

14
- 0032485451
- M. Satake, M. Fukui, A.-M. Legrand, P. Cruchet, and T. Yasumoto Tetrahedron Lett. 39 1998 1197 1198
- (1998) Tetrahedron Lett. , vol.39 , pp. 1197-1198
- Satake, M.¹ Fukui, M.² Legrand, A.-M.³ Cruchet, P.⁴ Yasumoto, T.⁵

15
- 0035976532
- M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, and M. Satake Science 294 2001 1904 1907
- (2001) Science , vol.294 , pp. 1904-1907
- Hirama, M.¹ Oishi, T.² Uehara, H.³ Inoue, M.⁴ Maruyama, M.⁵ Oguri, H.⁶ Satake, M.⁷

16
- 0037069719
- M. Inoue, H. Uehara, M. Maruyama, and Hirama Org. Lett. 4 2002 4551 4554
- (2002) Org. Lett. , vol.4 , pp. 4551-4554
- Inoue, M.¹ Uehara, H.² Maruyama, M.³ Hirama⁴

17
- 4344710277
- M. Inoue, K. Miyazaki, H. Uehara, M. Maruyama, and M. Hirama Proc. Natl. Acad. Sci. U.S.A. 101 2004 12013 12018
- (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 12013-12018
- Inoue, M.¹ Miyazaki, K.² Uehara, H.³ Maruyama, M.⁴ Hirama, M.⁵

18
- 1642320896
- M. Inoue, and M. Hirama Synlett 2004 577 595
- (2004) Synlett , pp. 577-595
- Inoue, M.¹ Hirama, M.²

19
- 11244250823
- M. Inoue, and M. Hirama Acc. Chem. Res. 37 2004 961 968
- (2004) Acc. Chem. Res. , vol.37 , pp. 961-968
- Inoue, M.¹ Hirama, M.²

20
- 24944570011
- M. Hirama Chem. Rec. 5 2005 240 250
- (2005) Chem. Rec. , vol.5 , pp. 240-250
- Hirama, M.¹

21
- 33746379107
- M. Inoue, K. Miyazaki, Y. Ishihara, A. Tatami, Y. Ohnuma, Y. Kawada, K. Komano, S. Yamashita, N. Lee, and M. Hirama J. Am. Chem. Soc. 128 2006 9352 9354
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 9352-9354
- Inoue, M.¹ Miyazaki, K.² Ishihara, Y.³ Tatami, A.⁴ Ohnuma, Y.⁵ Kawada, Y.⁶ Komano, K.⁷ Yamashita, S.⁸ Lee, N.⁹ Hirama, M.¹⁰

22
- 79953236568
- S. Yamashita, Y. Ishihara, H. Morita, J. Uchiyama, K. Takeuchi, M. Inoue, and M. Hirama J. Nat. Prod. 74 2011 357 364
- (2011) J. Nat. Prod. , vol.74 , pp. 357-364
- Yamashita, S.¹ Ishihara, Y.² Morita, H.³ Uchiyama, J.⁴ Takeuchi, K.⁵ Inoue, M.⁶ Hirama, M.⁷

23
- 0037532666
- H. Oguri, M. Hirama, T. Tsumuraya, I. Fujii, M. Maruyama, H. Uehara, and Y. Nagumo J. Am. Chem. Soc. 125 2003 7608 7612
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7608-7612
- Oguri, H.¹ Hirama, M.² Tsumuraya, T.³ Fujii, I.⁴ Maruyama, M.⁵ Uehara, H.⁶ Nagumo, Y.⁷

24
- 33747204080
- T. Tsumuraya, I. Fujii, M. Inoue, A. Tatami, K. Miyazaki, and M. Hirama Toxicon 48 2006 287 294
- (2006) Toxicon , vol.48 , pp. 287-294
- Tsumuraya, T.¹ Fujii, I.² Inoue, M.³ Tatami, A.⁴ Miyazaki, K.⁵ Hirama, M.⁶

25
- 77954231219
- T. Tsumuraya, I. Fujii, and M. Hirama Toxicon 56 2010 797 803
- (2010) Toxicon , vol.56 , pp. 797-803
- Tsumuraya, T.¹ Fujii, I.² Hirama, M.³

26
- 77954798010
- M. Isobe, and A. Hamajima Nat. Prod. Rep. 27 2010 1204 1226
- (2010) Nat. Prod. Rep. , vol.27 , pp. 1204-1226
- Isobe, M.¹ Hamajima, A.²

27
- 70349917819
- A. Hamajima, and M. Isobe Angew. Chem., Int. Ed. 48 2009 2941 2945
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 2941-2945
- Hamajima, A.¹ Isobe, M.²

28
- 2542442768
- H. Fuwa, S. Fujikawa, K. Tachibana, H. Takakura, and M. Sasaki Tetrahedron Lett. 45 2004 4795 4799
- (2004) Tetrahedron Lett. , vol.45 , pp. 4795-4799
- Fuwa, H.¹ Fujikawa, S.² Tachibana, K.³ Takakura, H.⁴ Sasaki, M.⁵

29
- 4444315238
- K. Fujiwara, A. Goto, D. Sato, Y. Ohtaniuchi, H. Tanaka, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 45 2004 7011 7014
- (2004) Tetrahedron Lett. , vol.45 , pp. 7011-7014
- Fujiwara, K.¹ Goto, A.² Sato, D.³ Ohtaniuchi, Y.⁴ Tanaka, H.⁵ Murai, A.⁶ Kawai, H.⁷ Suzuki, T.⁸

30
- 27644525252
- D. Domon, K. Fujiwara, Y. Ohtaniuchi, A. Takezawa, S. Takeda, H. Kawasaki, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 46 2005 8279 8283
- (2005) Tetrahedron Lett. , vol.46 , pp. 8279-8283
- Domon, D.¹ Fujiwara, K.² Ohtaniuchi, Y.³ Takezawa, A.⁴ Takeda, S.⁵ Kawasaki, H.⁶ Murai, A.⁷ Kawai, H.⁸ Suzuki, T.⁹

31
- 27644539378
- D. Domon, K. Fujiwara, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 46 2005 8285 8288
- (2005) Tetrahedron Lett. , vol.46 , pp. 8285-8288
- Domon, D.¹ Fujiwara, K.² Murai, A.³ Kawai, H.⁴ Suzuki, T.⁵

32
- 33745191187
- A. Takizawa, K. Fujiwara, E. Doi, A. Murai, H. Kawai, and T. Suzuki Tetrahedron 62 2006 7408 7435
- (2006) Tetrahedron , vol.62 , pp. 7408-7435
- Takizawa, A.¹ Fujiwara, K.² Doi, E.³ Murai, A.⁴ Kawai, H.⁵ Suzuki, T.⁶

33
- 33646441286
- A. Hamajima, and M. Isobe Org. Lett. 8 2006 1205 1208
- (2006) Org. Lett. , vol.8 , pp. 1205-1208
- Hamajima, A.¹ Isobe, M.²

34
- 34248684098
- A. Nonoyama, A. Hamajima, and M. Isobe Tetrahedron 63 2007 5886 5894
- (2007) Tetrahedron , vol.63 , pp. 5886-5894
- Nonoyama, A.¹ Hamajima, A.² Isobe, M.³

35
- 34250632393
- J.S. Clark, J. Conroy, and A.J. Blake Org. Lett. 9 2007 2091 2094
- (2007) Org. Lett. , vol.9 , pp. 2091-2094
- Clark, J.S.¹ Conroy, J.² Blake, A.J.³

36
- 38349141034
- A. Goto, K. Fujiwara, A. Kawai, H. Kawai, and T. Suzuki Org. Lett. 9 2007 5373 5376
- (2007) Org. Lett. , vol.9 , pp. 5373-5376
- Goto, A.¹ Fujiwara, K.² Kawai, A.³ Kawai, H.⁴ Suzuki, T.⁵

37
- 42949104563
- I. Kadota, T. Abe, M. Uni, H. Takamura, and Y. Yamamoto Tetrahedron Lett. 49 2008 3643 3647
- (2008) Tetrahedron Lett. , vol.49 , pp. 3643-3647
- Kadota, I.¹ Abe, T.² Uni, M.³ Takamura, H.⁴ Yamamoto, Y.⁵

38
- 68249123501
- I. Kadota, T. Abe, M. Uni, H. Takamura, and Y. Yamamoto Tetrahedron 65 2009 7784 7789
- (2009) Tetrahedron , vol.65 , pp. 7784-7789
- Kadota, I.¹ Abe, T.² Uni, M.³ Takamura, H.⁴ Yamamoto, Y.⁵

39
- 33847023052
- M. Inoue, F. Saito, M. Iwatsu, Y. Ishihara, and M. Hirama Tetrahedron Lett. 48 2007 2171 2175
- (2007) Tetrahedron Lett. , vol.48 , pp. 2171-2175
- Inoue, M.¹ Saito, F.² Iwatsu, M.³ Ishihara, Y.⁴ Hirama, M.⁵

40
- 79960955570
- S. Yamashita, N. Iijima, T. Shida, and M. Hirama Heterocycles 82 2010 761 774
- (2010) Heterocycles , vol.82 , pp. 761-774
- Yamashita, S.¹ Iijima, N.² Shida, T.³ Hirama, M.⁴

41
- 33847062466
- K. Yoshikawa, M. Inoue, and M. Hirama Tetrahedron Lett. 48 2007 2177 2180
- (2007) Tetrahedron Lett. , vol.48 , pp. 2177-2180
- Yoshikawa, K.¹ Inoue, M.² Hirama, M.³

42
- 33846286470
- M. Inoue, Y. Ishihara, S. Yamashita, and M. Hirama Org. Lett. 8 2006 5801 5804
- (2006) Org. Lett. , vol.8 , pp. 5801-5804
- Inoue, M.¹ Ishihara, Y.² Yamashita, S.³ Hirama, M.⁴

43
- 33846316751
- M. Inoue, S. Yamashita, Y. Ishihara, and M. Hirama Org. Lett. 8 2006 5805 5808
- (2006) Org. Lett. , vol.8 , pp. 5805-5808
- Inoue, M.¹ Yamashita, S.² Ishihara, Y.³ Hirama, M.⁴

44
- 0037015441
- M. Inoue, G.X. Wang, J. Wang, and M. Hirama Org. Lett. 4 2002 3439 3442
- (2002) Org. Lett. , vol.4 , pp. 3439-3442
- Inoue, M.¹ Wang, G.X.² Wang, J.³ Hirama, M.⁴

45
- 0037630668
- M. Inoue, J. Wang, G.X. Wang, Y. Ogasawara, and M. Hirama Tetrahedron 59 2003 5645 5659
- (2003) Tetrahedron , vol.59 , pp. 5645-5659
- Inoue, M.¹ Wang, J.² Wang, G.X.³ Ogasawara, Y.⁴ Hirama, M.⁵

46
- 4444328634
- S. Kobayashi, Y. Takahashi, K. Komano, B.H. Alizadeh, Y. Kawada, T. Oishi, S. Tanaka, Y. Ogasawara, S. Sasaki, and M. Hirama Tetrahedron 60 2004 8375 8396
- (2004) Tetrahedron , vol.60 , pp. 8375-8396
- Kobayashi, S.¹ Takahashi, Y.² Komano, K.³ Alizadeh, B.H.⁴ Kawada, Y.⁵ Oishi, T.⁶ Tanaka, S.⁷ Ogasawara, Y.⁸ Sasaki, S.⁹ Hirama, M.¹⁰

47
- 0344902741
- D.H.R. Barton, and S.W. McCombie J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
- (1975) J. Chem. Soc., Perkin Trans. 1 , pp. 1574-1585
- Barton, D.H.R.¹ McCombie, S.W.²

48
- 33751385486
- D.H.R. Barton, D.O. Jang, and J.C. Jaszberenyi J. Org. Chem. 58 1993 6838 6842
- (1993) J. Org. Chem. , vol.58 , pp. 6838-6842
- Barton, D.H.R.¹ Jang, D.O.² Jaszberenyi, J.C.³

49
- 0001325114
- M.J. Gaunt, J. Yu, and J.B. Spencer J. Org. Chem. 63 1998 4172 4173
- (1998) J. Org. Chem. , vol.63 , pp. 4172-4173
- Gaunt, M.J.¹ Yu, J.² Spencer, J.B.³

50
- 0034620235
- J. Xia, S.A. Abbas, R.D. Locke, C.F. Piskorz, J.L. Alderfer, and K.L. Matta Tetrahedron Lett. 41 2000 169 173
- (2000) Tetrahedron Lett. , vol.41 , pp. 169-173
- Xia, J.¹ Abbas, S.A.² Locke, R.D.³ Piskorz, C.F.⁴ Alderfer, J.L.⁵ Matta, K.L.⁶

51
- 0035844643
- J.A. Wright, J. Yu, and J.B. Spencer Tetrahedron Lett. 42 2001 4033 4036
- (2001) Tetrahedron Lett. , vol.42 , pp. 4033-4036
- Wright, J.A.¹ Yu, J.² Spencer, J.B.³

52
- 37049113039
- P.J. Garegg, and B. Sammuelsson J. Chem. Soc., Chem. Commun. 1979 978 980
- (1979) J. Chem. Soc., Chem. Commun. , pp. 978-980
- Garegg, P.J.¹ Sammuelsson, B.²

53
- 0001616071
- J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguchi Bull. Chem. Soc. Jpn. 52 1979 1989 1993
- (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1989-1993
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, T.⁴ Yamaguchi, M.⁵

54
- 0001268766
- V.H. Dahamukar, and S.D. Rychnovsky J. Org. Chem. 61 1996 8317 8320
- (1996) J. Org. Chem. , vol.61 , pp. 8317-8320
- Dahamukar, V.H.¹ Rychnovsky, S.D.²

55
- 0034804021
- I. Kadota, A. Ohno, K. Matsuda, and Y. Yamamoto J. Am. Chem. Soc. 123 2001 6702 6703
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6702-6703
- Kadota, I.¹ Ohno, A.² Matsuda, K.³ Yamamoto, Y.⁴

56
- 0001114396
- K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, and H. Yamamoto J. Am. Chem. Soc. 105 1983 2831 2843
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 2831-2843
- Maruoka, K.¹ Miyazaki, T.² Ando, M.³ Matsumura, Y.⁴ Sakane, S.⁵ Hattori, K.⁶ Yamamoto, H.⁷

57
- 0032580462
- M. Sasaki, M. Inoue, T. Noguchi, A. Takeichi, and K. Tachibana Tetrahedron Lett. 39 1998 2783 2786
- (1998) Tetrahedron Lett. , vol.39 , pp. 2783-2786
- Sasaki, M.¹ Inoue, M.² Noguchi, T.³ Takeichi, A.⁴ Tachibana, K.⁵

58
- 33845282956
- H. Kosugi, M. Kitaoka, K. Tagami, A. Takahashi, and H. Uda J. Org. Chem. 52 1987 1078 1082
- (1987) J. Org. Chem. , vol.52 , pp. 1078-1082
- Kosugi, H.¹ Kitaoka, M.² Tagami, K.³ Takahashi, A.⁴ Uda, H.⁵

59
- 84987584314
- G. Solladie, J. Hutt, and A. Girardin Synthesis 1987 173
- (1987) Synthesis , pp. 173
- Solladie, G.¹ Hutt, J.² Girardin, A.³

60
- 0002251804
- M. Zahouly, M. Journet, and M. Malacria Synlett 1994 366 368
- (1994) Synlett , pp. 366-368
- Zahouly, M.¹ Journet, M.² Malacria, M.³

61
- 3042833041
- G. Keum, S.B. Kang, Y. Kim, and E. Lee Org. Lett. 6 2004 1895 1897
- (2004) Org. Lett. , vol.6 , pp. 1895-1897
- Keum, G.¹ Kang, S.B.² Kim, Y.³ Lee, E.⁴

62
- 34548161417
- J.H. Jung, Y.W. Kim, M.A. Kim, S.Y. Choi, Y.K. Chung, T.-R. Kim, S. Shin, and E. Lee Org. Lett. 9 2007 3225 3228
- (2007) Org. Lett. , vol.9 , pp. 3225-3228
- Jung, J.H.¹ Kim, Y.W.² Kim, M.A.³ Choi, S.Y.⁴ Chung, Y.K.⁵ Kim, T.-R.⁶ Shin, S.⁷ Lee, E.⁸

63
- 36448929785
- T. Kimura, M. Hagiwara, and T. Nakata Tetrahedron Lett. 48 2007 9171 9175
- (2007) Tetrahedron Lett. , vol.48 , pp. 9171-9175
- Kimura, T.¹ Hagiwara, M.² Nakata, T.³

64
- 70349918263
- J.H. Jung, and E. Lee Angew. Chem., Int. Ed. 48 2009 5698 5700
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5698-5700
- Jung, J.H.¹ Lee, E.²

65
- 70449728293
- T. Kimura, M. Hagiwara, and T. Nakata Tetrahedron 65 2009 10893 10900
- (2009) Tetrahedron , vol.65 , pp. 10893-10900
- Kimura, T.¹ Hagiwara, M.² Nakata, T.³

66
- 2942576049
- For a recent review on Pummerer rearrangement, see: S.K. Bur, and A. Padwa Chem. Rev. 104 2004 2401 2432
- (2004) Chem. Rev. , vol.104 , pp. 2401-2432
- Bur, S.K.¹ Padwa, A.²

67
- 0001855961
- P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100 110
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 100-110
- Schwab, P.¹ Grubbs, R.H.² Ziller, J.W.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.