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1
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85031208524
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The Retinoids; Sporn, M. B.; Roberts, A. B.; Goodman, D. S., Eds.; Raven Press: New York, 1994 Chemistry and Biology of Synthetic Retinoids; Dawson, M. L.; Okamura, W. H., Eds.; CRC Press: Boca Raton Florida, 1990.
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0023913120
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Evans R.M. Science. 240:1998;889-895.
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Science
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Evans, R.M.1
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3
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0000874653
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Utrecht: VNU Science Press
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Hara R., Hara T., Ozaki K., Terakita A., Eguchi G., Kodama R., Takeuchi T. Retinal Proteins. 1987;VNU Science Press, Utrecht.
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(1987)
Retinal Proteins
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Hara, R.1
Hara, T.2
Ozaki, K.3
Terakita, A.4
Eguchi, G.5
Kodama, R.6
Takeuchi, T.7
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5
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0003590365
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John Wiley & Sons: New York
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The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1997. Some retinoid syntheses by olefin forming reactions, see: (a) Ito, M. Pure Appl. Chem. 1991, 63, 13-22; (b) Otera, J. In Carotenoids; Briton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Boston, 1996, pp. 103-114.
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(1997)
The Chemistry of Dienes and Polyenes
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Rappoport, Z.1
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6
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0001910358
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The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1997. Some retinoid syntheses by olefin forming reactions, see: (a) Ito, M. Pure Appl. Chem. 1991, 63, 13-22; (b) Otera, J. In Carotenoids; Briton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Boston, 1996, pp. 103-114.
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(1991)
Pure Appl. Chem.
, vol.63
, pp. 13-22
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Ito, M.1
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7
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0001181715
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Briton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Boston
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The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1997. Some retinoid syntheses by olefin forming reactions, see: (a) Ito, M. Pure Appl. Chem. 1991, 63, 13-22; (b) Otera, J. In Carotenoids; Briton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Boston, 1996, pp. 103-114.
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(1996)
Carotenoids
, pp. 103-114
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Otera, J.1
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8
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85031199625
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A mixture of stereoisomers was obtained generally.
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A mixture of stereoisomers was obtained generally.
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9
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85031207801
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Metal-Catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998 Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: New York, 2002; Vol. 1.
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12
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0032536552
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Uenishi J., Kawahama R., Yonemitsu O., Wada A., Ito M. Angew. Chem., Int. Ed. Engl. 37:1998;320-323.
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Angew. Chem., Int. Ed. Engl.
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Uenishi, J.1
Kawahama, R.2
Yonemitsu, O.3
Wada, A.4
Ito, M.5
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13
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0032922518
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Borhan B., Souto M.L., Um J.M., Zhou B., Nakanishi K. Chem. Eur. J. 5:1999;1172-1175.
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Chem. Eur. J.
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Borhan, B.1
Souto, M.L.2
Um, J.M.3
Zhou, B.4
Nakanishi, K.5
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14
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85031205117
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By Negishi et al. using bistrienylzinc reagent 1c for the synthesis of all trans retinal, see: Negishi, E.; Zbyslaw, O. Tetrahedron Lett. 1991, 32, 6683-6686 By Duchere and Parrain et al., using trienylstannane reagent 1b for the synthesis of all trans retinoic acid, see: Thibonnet, J.; Abarbri, M.; Duchene, A.; Parrain, J.-L. Synlett 1999, 141-143.
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15
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0034696967
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Stereodefined synthesis of (11Z)-retinal; see, Refs 6c,d and also Wada, A.; Fujioka, N.; Tanaka, Y.; Ito, M. J. Org. Chem. 2000, 65, 2438-2443. The report for 13-aryl substituted all trans retinal, see: Danshina, S. V.; Drachev, A. L.; Eremin, S. V.; Kaulen, A. D.; Khitrina, L. V.; Mitsner, B. I.; Belozerskii, A. N. Arch. Biochem. Biophys. 1990, 279, 225-231.
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J. Org. Chem.
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Wada, A.1
Fujioka, N.2
Tanaka, Y.3
Ito, M.4
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16
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0025368559
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Stereodefined synthesis of (11Z)-retinal; see, Refs 6c,d and also Wada, A.; Fujioka, N.; Tanaka, Y.; Ito, M. J. Org. Chem. 2000, 65, 2438-2443. The report for 13-aryl substituted all trans retinal, see: Danshina, S. V.; Drachev, A. L.; Eremin, S. V.; Kaulen, A. D.; Khitrina, L. V.; Mitsner, B. I.; Belozerskii, A. N. Arch. Biochem. Biophys. 1990, 279, 225-231.
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Arch. Biochem. Biophys.
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Dashina, S.V.1
Drachev, A.L.2
Eremin, S.V.3
Kaulen, A.D.4
Khitrina, L.V.5
Mitsner, B.I.6
Belozerskii, A.N.7
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18
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37049079705
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After work-up and successive purification by silica gel column chromatography, hardly separable proto-destannylated product and reagent derived by-products were largely contaminated with trienylstannane. In addition, it was found that the cross-coupling of 1b with 9 under the Stille conditions gave a mixture of geometric isomers at least by our hands.
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Stannylmagnesiation of enyne; Uenishi, J.; Kawahama, R.; Tanio, A.; Wakabayashi, S. Chem. Commun. 1993, 1438-1439. After work-up and successive purification by silica gel column chromatography, hardly separable proto-destannylated product and reagent derived by-products were largely contaminated with trienylstannane. In addition, it was found that the cross-coupling of 1b with 9 under the Stille conditions gave a mixture of geometric isomers at least by our hands.
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(1993)
Chem. Commun.
, pp. 1438-1439
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Uenishi, J.1
Kawahama, R.2
Tanio, A.3
Wakabayashi, S.4
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20
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85031196943
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2 and trimethylaluminum in the similar yield.
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2 and trimethylaluminum in the similar yield.
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21
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85031195515
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note
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f value of the boronic acid was 0.2 on silica gel TLC developed by 20% EtOAc in hexane). This boronic acid was used as THF solution in the next cross coupling reaction.
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22
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85031202690
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Compound 1a was usually used 2-3 equiv. for iodoalkene.
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Compound 1a was usually used 2-3 equiv. for iodoalkene.
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23
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85031207932
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Lera et al. reported Suzuki coupling of 9-demethyltrienylbronoic acid using TlOH conditions in Ref. 6a.
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Lera et al. reported Suzuki coupling of 9-demethyltrienylbronoic acid using TlOH conditions in Ref. 6a.
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24
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0031600116
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Recent literature: (a) Sakmar, T. P. Prog. Nucleic Acid Res. Mol. Biol. 1998, 59, 1-34; (b) Borhan, B.; Souto, M. L.; Imai, H.; Shichida, Y.; Nakanishi, K. Science 2000, 288, 2209-2212. (b) Borhan, B.; Souto, M. L.; Imai, H.; Shichida, Y.; Nakanishi, K. Science 2000, 288, 2209-2212.
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Prog. Nucleic Acid Res. Mol. Biol.
, vol.59
, pp. 1-34
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Sakmar, T.P.1
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25
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0034705612
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Recent literature: (a) Sakmar, T. P. Prog. Nucleic Acid Res. Mol. Biol. 1998, 59, 1-34; (b) Borhan, B.; Souto, M. L.; Imai, H.; Shichida, Y.; Nakanishi, K. Science 2000, 288, 2209-2212.
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(2000)
Science
, vol.288
, pp. 2209-2212
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Borhan, B.1
Souto M., L.2
Imai, H.3
Shichida, Y.4
Nakanishi, K.5
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26
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0034604451
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Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Trong I.L., Teller D.C., Okada T., Stenkamp R.E., Yamamoto M., Miyano M. Science. 289:2000;739-745.
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(2000)
Science
, vol.289
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Palczewski, K.1
Kumasaka, T.2
Hori, T.3
Behnke, C.A.4
Motoshima, H.5
Fox, B.A.6
Trong, I.L.7
Teller, D.C.8
Okada, T.9
Stenkamp, R.E.10
Yamamoto, M.11
Miyano, M.12
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27
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0032478163
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For the case of 9-alkyl substituted (11Z)-retinal, see:
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For the case of 9-alkyl substituted (11Z)-retinal, see: Wada A., Fujioka N., Imai H., Shichida Y., Ito M. Bioorg. Med. Chem. Lett. 8:1998;423-426.
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(1998)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 423-426
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Wada, A.1
Fujioka, N.2
Imai, H.3
Shichida, Y.4
Ito, M.5
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30
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85031208058
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note
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6) δ 9.73 (1H, d, J=8.1 Hz), 7.43 (2H, d, J=8.1 Hz), 7.06 (2H, d, J=8.1 Hz), 6.52 (1H, t, J=12.1 Hz), 6.35 (1H, d, J=8.1 Hz), 6.27 (1H, d, J=15.8 Hz), 5.94 (1H, d, J=12.1 Hz), 5.86 (1H, d, J=15.8 Hz), 5.81 (1H, d, J=12.1 Hz), 5.35 (1H, s), 3.19 (6H, s), 1.93 (2H, t, J=6.2 Hz), 1.71 (3H, s), 1.67 (3H, s), 1.63-1.50 (2H, m), 1.47-1.41 (2H, m), 1.04 (6H, s).
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