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85008014440
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Although okadaic acid was isolated from marine sponges, contaminating dinoflagellates are responsible for the production of this toxin. Murakami, Y.; Oshima, Y.; Yasumoto, T. Bull. Japan Soc. Sci. Fish., 1982, 48, 69. For an excellent review on Ciguatera and its off-shoots, see. Scheuer, P.J. Tetrahedron, 1994, 50, 3.
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Although okadaic acid was isolated from marine sponges, contaminating dinoflagellates are responsible for the production of this toxin. Murakami, Y.; Oshima, Y.; Yasumoto, T. Bull. Japan Soc. Sci. Fish., 1982, 48, 69. For an excellent review on Ciguatera and its off-shoots, see. Scheuer, P.J. Tetrahedron, 1994, 50, 3.
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0025181418
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Cohen, P.; Holmes, C.F.B.; Tsukitani, Y. Trends Biochem. Sci., 1990, 15, 98. See also: Brugge, J.S. Chem. Biol., 1994, introductory issue.
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0000646016
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0001763264
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See also: (a) Wei, Z.Y.; Li, J.S.; Wang, D.; Chan, T.H. Tetrahedron Lett., 1987, 28, 3441;
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Wei, Z.Y.1
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15
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0343298513
-
-
note
-
4, followed by opening of the heterocycle generates the oxonium ion 21 which is then intercepted by the incipient allylic residue. (Formula Represented)
-
-
-
-
16
-
-
0343734174
-
-
note
-
The observed stereochemistry corroborates the observations of Taddei and Ricci and is easily deduced from the analysis of the NMR spectra of compounds 12. It originates from the chair-like transition state 21.
-
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17
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0043178014
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(a) Hutchins, R.O.; Hoke, D.; Keogh, J.; Koharski, D. Tetrahedron Lett., 1969, 3495;
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0000837348
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(b) Hutchins, R.O.; Kandasamy, D.; Dux III, F.; Maryanoff, C.A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem., 1978, 43, 2259.
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84916002157
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21
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0029038995
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22
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0343298511
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-
This failure was also noticed by Taddei and Ricci (Taddei, M., Personal communication)
-
This failure was also noticed by Taddei and Ricci (Taddei, M., Personal communication).
-
-
-
-
23
-
-
0343734171
-
-
note
-
2 = 4.4 Hz) in compounds 10, thus unambiguously positioning the choride and methyl substituents in an equatorial and axial position respectively.
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-
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24
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0001044675
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(a) Yamamoto Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem., 1984, 49, 1096;
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0000841861
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(b) Yamamoto Y.; Saito, Y.; Maruyama, K. J. Organometallic Chem., 1985, 292, 311.
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Yamamoto, Y.1
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Maruyama, K.3
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