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Reviews: (b) Parsons, A. F. Tetrahedron 1996, 52, 4149. For selected recently syntheses: (c) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727. (f) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (g) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467. (h) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139. (i) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 19, 3194. (j) Hirasawa, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 7587.
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Reviews: (b) Parsons, A. F. Tetrahedron 1996, 52, 4149. For selected recently syntheses: (c) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727. (f) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (g) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467. (h) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139. (i) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 19, 3194. (j) Hirasawa, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 7587.
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Reviews: (b) Parsons, A. F. Tetrahedron 1996, 52, 4149. For selected recently syntheses: (c) Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727. (f) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (g) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467. (h) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139. (i) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 19, 3194. (j) Hirasawa, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 7587.
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17
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7044246766
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note
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This synthetic route could be also applicable for the synthesis of (-)-domoic acid by modifying precursor A with a dienoic side chain.
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18
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0026618606
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N-Benzylation was carried out first by reductive animation; see: Barco, A.; Benetti, S.; Spalluto, G. J. Org. Chem. 1992, 57, 6279.
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19
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7044238039
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note
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4) unsuccessfully.
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20
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7044228749
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note
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Synthesized from hydroxyacetone in 67% overall yield over four steps: silylation followed by Horner - Wadsworth - Emmons reaction, 1,2-reduction of the ester moiety, and bromination.
-
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21
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7044240226
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note
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(-)-MPTA ester 10 was derived from racemic and enantiomerically enriched 9 by esterification using (-)-MPTACl in 70% overall yield.
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22
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0001178865
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Deiters, A.; Mück-Lichtenfeld, C.; Fröhlich, R.; Hoppe, D. Org. Lett. 2000, 2, 2415.
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Hoppe, D.4
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23
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7044250358
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note
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Other conditions for the asymmetric cyclization, as well as other key precursors, were tried with less success.
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-
-
24
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7044232572
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(a) Kondo, K.; Kondo, Y.; Takemoto, T.; Kenoue, T. Bull. Chem. Soc. Jpn. 1962, 35, 1899.
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25
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7044248673
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note
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(b) For a discussion of the rotameric distributions of several kainoids:
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26
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0021364566
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(c) Conway, G. A.; Park, J. S.; Maggiora, L.; Mertes, M. P.; Galton, N.; Michaelis, E. K. J. Med. Chem. 1984, 27, 52.
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0003909854
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Georg Thieme Verlag Stuttgart: New York
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NMR-Spectroscopie; Günther, H., Ed.; Georg Thieme Verlag Stuttgart: New York, 1992. The coupling constants were obtained with the use of the packet of programs TURBOMOLE (version 5.6) (University Karlsruhe: Karlsruhe, Germany, 2003). The structures were optimized with the theoretical function at the DFT level using the pure B-P functional [DFT-(B-P)] and the basis set TZVP (triple-valence-polarized).
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(1992)
NMR-Spectroscopie
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Günther, H.1
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29
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0000163012
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In all known examples, deprotonation of O-allylic carbamates with n-BuLi/sp led to the (S)-configured organolithium compound. For reviews: (a) Hoppe, D. Angw. Chem. 1984, 96, 930; Angw. Chem., Int. Ed. Engl. 1984, 23, 932. (b) Hoppe, D.; Hense, T. Angw. Chem., Int. Ed. Engl. 1997, 36, 2282 and references therein.
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Hoppe, D.1
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0042402792
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In all known examples, deprotonation of O-allylic carbamates with n-BuLi/sp led to the (S)-configured organolithium compound. For reviews: (a) Hoppe, D. Angw. Chem. 1984, 96, 930; Angw. Chem., Int. Ed. Engl. 1984, 23, 932. (b) Hoppe, D.; Hense, T. Angw. Chem., Int. Ed. Engl. 1997, 36, 2282 and references therein.
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31
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0030694010
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and references therein
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In all known examples, deprotonation of O-allylic carbamates with n-BuLi/sp led to the (S)-configured organolithium compound. For reviews: (a) Hoppe, D. Angw. Chem. 1984, 96, 930; Angw. Chem., Int. Ed. Engl. 1984, 23, 932. (b) Hoppe, D.; Hense, T. Angw. Chem., Int. Ed. Engl. 1997, 36, 2282 and references therein.
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N reactions, see: Magid, M. R. Tetrahedron 1980, 31, 1901.
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(b) Grieco, A. P.; Oguri, T.; Yokoyama, Y. Org. Lett. 1978, 5, 419.
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Seppi, M.; Kalkofen, R.; Reupohl, J.; Fröhlich, R.; Hoppe, D. Angew. Chem. 2004, 116, 1447.
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Hoppe, D.5
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40
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7044223798
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note
-
1H NMR exhibits two broad singlets at 4.62 and 4.91 ppm for the alkene protons, indicating the C3-C4 cis relationship (see refences 4i and 12). The NOE studies were carried out at low temperature because of the broad signals.
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