-
2
-
-
0024815125
-
-
Ciguatoxin CTX1B: M. Murata, A.-M. Legrand, Y. Ishibashi, M. Fukui, and T. Yasumoto J. Am. Chem. Soc. 111 1989 8929
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 8929
-
-
Murata, M.1
Legrand, A.-M.2
Ishibashi, Y.3
Fukui, M.4
Yasumoto, T.5
-
3
-
-
0025045174
-
-
M. Murata, A.-M. Legrand, Y. Ishibashi, M. Fukui, and T. Yasumoto J. Am. Chem. Soc. 112 1990 4380
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4380
-
-
Murata, M.1
Legrand, A.-M.2
Ishibashi, Y.3
Fukui, M.4
Yasumoto, T.5
-
5
-
-
0001377493
-
-
For reviews of ciguatoxins and related marine toxins, see: Y. Shimizu Chem. Rev. 93 1993 1685
-
(1993)
Chem. Rev.
, vol.93
, pp. 1685
-
-
Shimizu, Y.1
-
10
-
-
0021251109
-
-
J.-N. Bidard, H.P.M. Vijverberg, C. Frelin, E. Chungue, A.-M. Legrand, R. Bagnis, and M. Lazdanski J. Biol. Chem. 259 1984 8353
-
(1984)
J. Biol. Chem.
, vol.259
, pp. 8353
-
-
Bidard, J.-N.1
Vijverberg, H.P.M.2
Frelin, C.3
Chungue, E.4
Legrand, A.-M.5
Bagnis, R.6
Lazdanski, M.7
-
15
-
-
0035976532
-
-
Total synthesis of CTX3C: M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, and M. Satake Science 294 2001 1904
-
(2001)
Science
, vol.294
, pp. 1904
-
-
Hirama, M.1
Oishi, T.2
Uehara, H.3
Inoue, M.4
Maruyama, M.5
Oguri, H.6
Satake, M.7
-
17
-
-
0037017773
-
-
M. Maruyama, M. Inoue, T. Oishi, H. Oguri, Y. Ogasawara, Y. Shindo, and M. Hirama Tetrahedron 58 2002 1835
-
(2002)
Tetrahedron
, vol.58
, pp. 1835
-
-
Maruyama, M.1
Inoue, M.2
Oishi, T.3
Oguri, H.4
Ogasawara, Y.5
Shindo, Y.6
Hirama, M.7
-
18
-
-
0037026010
-
-
H. Uehara, T. Oishi, M. Inoue, M. Shoji, Y. Nagumo, M. Kosaka, J.-Y. Le Brazidec, and M. Hirama Tetrahedron 58 2002 6493
-
(2002)
Tetrahedron
, vol.58
, pp. 6493
-
-
Uehara, H.1
Oishi, T.2
Inoue, M.3
Shoji, M.4
Nagumo, Y.5
Kosaka, M.6
Le Brazidec, J.-Y.7
Hirama, M.8
-
19
-
-
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
-
(2004)
Tetrahedron
, vol.60
, pp. 8375
-
-
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
-
20
-
-
1842739309
-
-
M. Inoue, S. Yamashita, A. Tatami, K. Miyazaki, and M. Hirama J. Org. Chem. 69 2004 2797
-
(2004)
J. Org. Chem.
, vol.69
, pp. 2797
-
-
Inoue, M.1
Yamashita, S.2
Tatami, A.3
Miyazaki, K.4
Hirama, M.5
-
22
-
-
4344710277
-
-
M. Inoue, K. Miyazaki, H. Uehara, M. Maruyama, and M. Hirama Proc. Natl. Sci. Acad. U.S.A. 101 2004 12013
-
(2004)
Proc. Natl. Sci. Acad. U.S.A.
, vol.101
, pp. 12013
-
-
Inoue, M.1
Miyazaki, K.2
Uehara, H.3
Maruyama, M.4
Hirama, M.5
-
24
-
-
1642325006
-
-
Recent synthetic studies on ciguatoxins by other groups: S. Kobayashi, B.H. Alizadeh, S.-y. Sasaki, H. Oguri, and M. Hirama Org. Lett. 6 2004 751
-
(2004)
Org. Lett.
, vol.6
, pp. 751
-
-
Kobayashi, S.1
Alizadeh, B.H.2
Sasaki, S.-Y.3
Oguri, H.4
Hirama, M.5
-
27
-
-
2542442768
-
-
H. Fuwa, S. Fujikawa, K. Tachibana, H. Takakura, and M. Sasaki Tetrahedron Lett. 45 2004 4795
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 4795
-
-
Fuwa, H.1
Fujikawa, S.2
Tachibana, K.3
Takakura, H.4
Sasaki, M.5
-
30
-
-
18244380593
-
-
M.L. Candenas, F.J. Pinto, C.G. Cintada, E.Q. Morales, I. Brouard, M.T. Díaz, M. Rico, E. Rodríguez, R.M. Rodríguez, R. Pérez, R.L. Pérez, and J.D. Martín Tetrahedron 58 2002 1921
-
(2002)
Tetrahedron
, vol.58
, pp. 1921
-
-
Candenas, M.L.1
Pinto, F.J.2
Cintada, C.G.3
Morales, E.Q.4
Brouard, I.5
Díaz, M.T.6
Rico, M.7
Rodríguez, E.8
Rodríguez, R.M.9
Pérez, R.10
Pérez, R.L.11
Martín, J.D.12
-
37
-
-
0035039187
-
-
K. Fujiwara, D. Takaoka, K. Kusumi, K. Kawai, and A. Murai Synlett 2001 691
-
(2001)
Synlett
, pp. 691
-
-
Fujiwara, K.1
Takaoka, D.2
Kusumi, K.3
Kawai, K.4
Murai, A.5
-
38
-
-
0036373850
-
-
K. Fujiwara, Y. Koyama, E. Doi, K. Shimawaki, Y. Ohtaniuchi, A. Takemura, S. Souma, and A. Murai Synlett 2002 1496
-
(2002)
Synlett
, pp. 1496
-
-
Fujiwara, K.1
Koyama, Y.2
Doi, E.3
Shimawaki, K.4
Ohtaniuchi, Y.5
Takemura, A.6
Souma, S.7
Murai, A.8
-
39
-
-
0036427428
-
-
K. Fujiwara, Y. Koyama, K. Kawai, H. Tanaka, and A. Murai Synlett 2002 1835
-
(2002)
Synlett
, pp. 1835
-
-
Fujiwara, K.1
Koyama, Y.2
Kawai, K.3
Tanaka, H.4
Murai, A.5
-
41
-
-
4444315238
-
-
K. Fujiwara, A. Goto, D. Sato, Y. Ohtaniuchi, H. Tanaka, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 45 2004 7011
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 7011
-
-
Fujiwara, K.1
Goto, A.2
Sato, D.3
Ohtaniuchi, Y.4
Tanaka, H.5
Murai, A.6
Kawai, H.7
Suzuki, T.8
-
42
-
-
4644235621
-
-
A. Takemura, K. Fujiwara, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 45 2004 7567
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 7567
-
-
Takemura, A.1
Fujiwara, K.2
Murai, A.3
Kawai, H.4
Suzuki, T.5
-
43
-
-
21944455143
-
-
A. Takemura, K. Fujiwara, K. Shimawaki, A. Murai, H. Kawai, and T. Suzuki Tetrahedron 61 2005 7392
-
(2005)
Tetrahedron
, vol.61
, pp. 7392
-
-
Takemura, A.1
Fujiwara, K.2
Shimawaki, K.3
Murai, A.4
Kawai, H.5
Suzuki, T.6
-
44
-
-
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
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 8279
-
-
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
-
45
-
-
27644539378
-
-
D. Domon, K. Fujiwara, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 46 2005 8285
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 8285
-
-
Domon, D.1
Fujiwara, K.2
Murai, A.3
Kawai, H.4
Suzuki, T.5
-
47
-
-
0037453554
-
-
A similar ring closure of the G-ring part by reductive etherification was reported by the Isobe group, where the cyclization of a tricyclic compound corresponding to the EF-H-ring part having 26-keto and 31-hydroxy groups was successfully performed: S. Takai, N. Sawada, and M. Isobe J. Org. Chem. 68 2003 3225
-
(2003)
J. Org. Chem.
, vol.68
, pp. 3225
-
-
Takai, S.1
Sawada, N.2
Isobe, M.3
-
48
-
-
0034644383
-
-
Although the use of the cis-epoxide (C29-epi-4 ) corresponding to 4 might be straightforward and exclude the C29-inversion step, the cis-epoxide could not be prepared so far because of the difficulty in the synthesis of the Z-iodoalkene corresponding to 6. For successful synthesis of a Z-iodoalkene, see: A.B. Smith III, T.J. Beauchamp, M.J. LaMarche, M.D. Kaufman, Y. Qiu, H. Arimoto, D.R. Jones, and K. Kobayashi J. Am. Chem. Soc. 122 2000 8654
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8654
-
-
Smith III, A.B.1
Beauchamp, T.J.2
Lamarche, M.J.3
Kaufman, M.D.4
Qiu, Y.5
Arimoto, H.6
Jones, D.R.7
Kobayashi, K.8
-
51
-
-
0025980596
-
-
Cf. K.C. Nocolaou, C.A. Veale, C.-K. Hwang, J. Hutchinson, C.V.C. Prasad, and W.W. Ogilvie Angew. Chem., Int. Ed. Engl. 30 1991 299
-
(1991)
Angew. Chem., Int. Ed. Engl.
, vol.30
, pp. 299
-
-
Nocolaou, K.C.1
Veale, C.A.2
Hwang, C.-K.3
Hutchinson, J.4
Prasad, C.V.C.5
Ogilvie, W.W.6
-
61
-
-
2142858450
-
-
Since the R-configuration at C31 of 25 was proved by modified Mosher's method, the C31-configuration of the other diastereomer 24 was determined as S. For modified Mosher's method, see: I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 4092
-
-
Ohtani, I.1
Kusumi, T.2
Kashman, Y.3
Kakisawa, H.4
-
62
-
-
29644442511
-
-
note
-
The reduction of the ketone prepared from 25 was examined with several reductants, where L-Selectride® gave the best yield and selectivity of 24. The results also suggested that the selectivity of 24 increased with increasing bulkiness of the reductant. However, the reasons for the high stereoselectivity and the stereochemical preference in the reduction with bulky reductants were unclear.
-
-
-
-
63
-
-
0016386657
-
-
S. Tanaka, H. Yamamoto, H. Nozaki, K.B. Sharpless, R.C. Michaelson, and J.D. Cutting J. Am. Chem. Soc. 96 1974 5254
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 5254
-
-
Tanaka, S.1
Yamamoto, H.2
Nozaki, H.3
Sharpless, K.B.4
Michaelson, R.C.5
Cutting, J.D.6
-
65
-
-
29644442250
-
-
note
-
The net product ratio of 32 to 31 from 30 was determined as 2:1 by the reduction of pure 30, prepared alternatively, under the same conditions.
-
-
-
-
67
-
-
0034620235
-
-
J. Xia, S.A. Abbas, R.D. Locke, C.F. Piskorz, J.L. Alderfer, and K.L. Matta Tetrahedron Lett. 41 2000 169
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 169
-
-
Xia, J.1
Abbas, S.A.2
Locke, R.D.3
Piskorz, C.F.4
Alderfer, J.L.5
Matta, K.L.6
-
69
-
-
29644448309
-
-
note
-
+]: 1078.3230, found: 1078.3217.
-
-
-
|