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10
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0031550831
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The absolute stereochemistry of ciguatoxin was determined to be that represented by structure 1; see a) H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto, N. Harada, Tetrahedron 1997, 53, 3057-3072; b) M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada, T. Yasumoto, J. Am. Chem. Soc. 1997, 119, 11325-11326.
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11
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0030670907
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The absolute stereochemistry of ciguatoxin was determined to be that represented by structure 1; see a) H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto, N. Harada, Tetrahedron 1997, 53, 3057-3072; b) M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada, T. Yasumoto, J. Am. Chem. Soc. 1997, 119, 11325-11326.
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Eds.: Y. Hokama, P.J. Scheuer, T. Yasumoto, Asian-Pacific Research Foundation, Honolulu
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c) M. Sasaki, M. Inoue, M. Murata, K. Tachibana in Proceedings of the International Symposium on Ciguatera and Marine Natural Products (Eds.: Y. Hokama, P.J. Scheuer, T. Yasumoto), Asian-Pacific Research Foundation, Honolulu, 1995, pp. 229-237;
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Recent reviews: a) E. Alvarez, M.-L. Candenas, R. Pérez, J. L. Ravelo, J. D. Martín, Chem. Rev. 1995, 95, 1953-1980; b) Y. Mori, Chem. Eur. J. 1997, 3, 849-852.
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Recent reviews: a) E. Alvarez, M.-L. Candenas, R. Pérez, J. L. Ravelo, J. D. Martín, Chem. Rev. 1995, 95, 1953-1980; b) Y. Mori, Chem. Eur. J. 1997, 3, 849-852.
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31
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0030821537
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Recently, a new synthetic method was reported for the construction of the nine-membered ether ring, together with an application of the method to synthesis of the EFGH ring skeleton of brevetoxin A: K. C. Nicolaou, Z. Yang, M. Ouellette, G.-Q. Shi, P. Gärtner, J. L. Gunzner, K. A. Agrios, R. Huber, R. Chadha, D. H. Huang, J. Am. Chem. Soc. 1997, 119, 8105-8106.
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Huber, R.8
Chadha, R.9
Huang, D.H.10
-
32
-
-
0344623904
-
-
note
-
The numbering of carbon atoms in all compounds in this communication corresponds to that of ciguatoxin.
-
-
-
-
33
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33845182977
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K. C. Nicolaou, C. V. C. Prasad, C-K. Hwang, M. E. Duggan, C. A. Veale, J. Am. Chem. Soc. 1989, 111, 5321-5330.
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Veale, C.A.5
-
34
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0029811112
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2SiCl, imidazole, DMF, 60°C; g) NaOMe, MeOH, RT, 69% over four steps.
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0027530713
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b) V. Gevorgyan, I. Kadota, Y. Yamamoto, ibid. 1993, 34, 1313-1316;
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0001222006
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39
-
-
0345054434
-
-
note
-
Use of 10-camphorsulfonic acid as an acid catalyst in this acetalization gave a 1:1 mixture of acetals 10.
-
-
-
-
40
-
-
0344623902
-
-
note
-
When chlorotrimethylsilane was used as silylating agent, a significant amount (10-20% yield) of α-alkoxyallylsilane was formed as a byproduct.
-
-
-
-
41
-
-
85033540923
-
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I. Kadota, V. Gevorgyan, J. Yamada, Y. Yamamoto, Synlett 1991, 823-824.
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Kadota, I.1
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Yamamoto, Y.4
-
42
-
-
0345054436
-
-
note
-
From the corresponding γ-alkoxyallyltrimethylsilane, cyclization of the β-H isomer gave the desired (23S,24A)-5 in 42% yield as the major product together with its (23R,24R) diastereoisomer (30%), whereas cyclization of the α-H isomer produced 5 in only 29% yield together with three other stereoisomers for C23 and C24 in yields of 28, 27, and 13%.
-
-
-
-
43
-
-
0345486074
-
-
note
-
The configuration at C27 of 14 was assigned on the basis of strong NOEs between 24-H/27-H and 27-H/29-H. The syn relationship between 23-H and 30-H was also confirmed by NOE experiments.
-
-
-
-
44
-
-
0345054437
-
-
note
-
β-Acetoxy ketone 14 underwent partial β-elimination during chromatography over silica gel to yield the α,β-unsaturated ketone.
-
-
-
-
45
-
-
0000643506
-
-
K. Nozaki, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1990, 63, 2578-2583.
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(1990)
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Nozaki, K.1
Oshima, K.2
Utimoto, K.3
-
46
-
-
0344192186
-
-
note
-
The syn relationship between 36-H and 42-H in compound 21 was unambiguously established by NOE experiments.
-
-
-
-
48
-
-
0345486073
-
-
note
-
+]: 783.4295, found: 783.4285.
-
-
-
|