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R. R. Birge, Annu. Rev. Biophys. Bioeng. 1981, 10, 315-354; J.E. Dowling, The Retina, Harvard University Press, Cambridge, 1987.
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K. Nakanishi, R. Crouch, Isr. J. Chem. 1995, 35, 235-272; R. R. Rando, Angew. Chem. 1990, 102, 507-526; Angew. Chem. Int. Ed. Engl. 1990, 29, 461-480; J. C. Saari, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann), Raven, New York, 1994, chap. 9, pp. 351-395.
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K. Nakanishi, R. Crouch, Isr. J. Chem. 1995, 35, 235-272; R. R. Rando, Angew. Chem. 1990, 102, 507-526; Angew. Chem. Int. Ed. Engl. 1990, 29, 461-480; J. C. Saari, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann), Raven, New York, 1994, chap. 9, pp. 351-395.
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Rando, R.R.1
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0025298101
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K. Nakanishi, R. Crouch, Isr. J. Chem. 1995, 35, 235-272; R. R. Rando, Angew. Chem. 1990, 102, 507-526; Angew. Chem. Int. Ed. Engl. 1990, 29, 461-480; J. C. Saari, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann), Raven, New York, 1994, chap. 9, pp. 351-395.
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0002463912
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Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann, Raven, New York, chap. 9
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K. Nakanishi, R. Crouch, Isr. J. Chem. 1995, 35, 235-272; R. R. Rando, Angew. Chem. 1990, 102, 507-526; Angew. Chem. Int. Ed. Engl. 1990, 29, 461-480; J. C. Saari, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann), Raven, New York, 1994, chap. 9, pp. 351-395.
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Saari, J.C.1
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0021225009
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Reviews
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Reviews: R. S. H. Liu, A. E. Asato, Tetrahedron 1984, 40, 1931-1969; M. Dawson, P. D. Hobbs, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann), Raven, New York, 1994, chap. 2, pp. 5-178; recent synthesis of (11Z)-retinals: B. Borhan, R. Kunz, A. Y. Wang, K. Nakanishi, N. Bojkova, K. Yoshihara, J. Am. Chem. Soc. 1997, 119, 5758-5759; A. Wada, Y. Tanaka, N. Fujioka, M. Ito, Bioorg. Med. Chem. Lett. 1996, 6, 2049-2052, and references therein.
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Tetrahedron
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Liu, R.S.H.1
Asato, A.E.2
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8
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0001980367
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Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann, Raven, New York, chap. 2
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Reviews: R. S. H. Liu, A. E. Asato, Tetrahedron 1984, 40, 1931-1969; M. Dawson, P. D. Hobbs, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann), Raven, New York, 1994, chap. 2, pp. 5-178; recent synthesis of (11Z)-retinals: B. Borhan, R. Kunz, A. Y. Wang, K. Nakanishi, N. Bojkova, K. Yoshihara, J. Am. Chem. Soc. 1997, 119, 5758-5759; A. Wada, Y. Tanaka, N. Fujioka, M. Ito, Bioorg. Med. Chem. Lett. 1996, 6, 2049-2052, and references therein.
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Dawson, M.1
Hobbs, P.D.2
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9
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0030761584
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recent synthesis of (11Z)-retinals
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Reviews: R. S. H. Liu, A. E. Asato, Tetrahedron 1984, 40, 1931-1969; M. Dawson, P. D. Hobbs, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann), Raven, New York, 1994, chap. 2, pp. 5-178; recent synthesis of (11Z)-retinals: B. Borhan, R. Kunz, A. Y. Wang, K. Nakanishi, N. Bojkova, K. Yoshihara, J. Am. Chem. Soc. 1997, 119, 5758-5759; A. Wada, Y. Tanaka, N. Fujioka, M. Ito, Bioorg. Med. Chem. Lett. 1996, 6, 2049-2052, and references therein.
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Borhan, B.1
Kunz, R.2
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Nakanishi, K.4
Bojkova, N.5
Yoshihara, K.6
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0030567869
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and references therein
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Reviews: R. S. H. Liu, A. E. Asato, Tetrahedron 1984, 40, 1931-1969; M. Dawson, P. D. Hobbs, The Retinoids, Biology, Chemistry and Medicine, 2nd ed. (Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann), Raven, New York, 1994, chap. 2, pp. 5-178; recent synthesis of (11Z)-retinals: B. Borhan, R. Kunz, A. Y. Wang, K. Nakanishi, N. Bojkova, K. Yoshihara, J. Am. Chem. Soc. 1997, 119, 5758-5759; A. Wada, Y. Tanaka, N. Fujioka, M. Ito, Bioorg. Med. Chem. Lett. 1996, 6, 2049-2052, and references therein.
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J. Uenishi, R. Kawahama, O. Yonemitsu, J. Tsuji, J. Org. Chem. 1996, 61, 5716-5717; J. Uenishi, R. Kawahama, Y. Shiga. O. Yonemitsu, J. Tsuji, Tetrahedron Lett. 1996, 37, 6759-6762.
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R. W. Dugger, C H. Heathcock, Syn. Commun, 1980, 10, 509-515; J. A. Pardoen, P. P. Mulder, E. M. M. van Den Berg, J. Lugtenburg, Can, J. Chem. 1985, 63, 1431-1435; A. Wada, S. Hiraishi, M. Ito, Chem. Pharm. Bull. 1994, 42, 757-759.
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R. W. Dugger, C H. Heathcock, Syn. Commun, 1980, 10, 509-515; J. A. Pardoen, P. P. Mulder, E. M. M. van Den Berg, J. Lugtenburg, Can, J. Chem. 1985, 63, 1431-1435; A. Wada, S. Hiraishi, M. Ito, Chem. Pharm. Bull. 1994, 42, 757-759.
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17
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0347397269
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note
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3): δ = 9.0, 13.6,19.3, 27.3, 29.1, 58.8, 139.3, 142.3.
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19
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33947473632
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F. Ramirez, N. B. Desai, N. McKelvie, J. Am. Chem. Soc. 1962, 84, 1745-1747.
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Ramirez, F.1
Desai, N.B.2
McKelvie, N.3
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20
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0346766757
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note
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1H NMR spectroscopy for a mixture of 8 and the unseparable by-product 10-bromo-3,5,7,9-tetraene (retroionylidene bromide), which results from direct bromination of 4 under the reaction conditions. However, the by-product decomposed easily within several hours at room temperature.
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22
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0347397268
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(E)-l-[3-(tert-Butyldimethylsilyl)oxy-l-propenyl]-l,3,2-benzodioxaborole could be used instead of the boronic acid for this reaction
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(E)-l-[3-(tert-Butyldimethylsilyl)oxy-l-propenyl]-l,3,2-benzodioxaborole could be used instead of the boronic acid for this reaction.
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23
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0348028032
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note
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++H): 271, 2062; found: 271.2068.
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25
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0346766756
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note
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+): 268.1826; found: 268.1814.
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