메뉴 건너뛰기




Volumn 37, Issue 3, 1998, Pages 320-323

Stereocontrolled Synthesis of (11Z)-Retinal and Its Analogues

Author keywords

Alkenes; Bioorganic chemistry; Cross coupling; Palladium; Retinoids

Indexed keywords


EID: 0032536552     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<320::AID-ANIE320>3.0.CO;2-4     Document Type: Article
Times cited : (57)

References (25)
  • 1
    • 0019349025 scopus 로고
    • R. R. Birge, Annu. Rev. Biophys. Bioeng. 1981, 10, 315-354; J.E. Dowling, The Retina, Harvard University Press, Cambridge, 1987.
    • (1981) Annu. Rev. Biophys. Bioeng. , vol.10 , pp. 315-354
    • Birge, R.R.1
  • 2
    • 0019349025 scopus 로고
    • Harvard University Press, Cambridge
    • R. R. Birge, Annu. Rev. Biophys. Bioeng. 1981, 10, 315-354; J.E. Dowling, The Retina, Harvard University Press, Cambridge, 1987.
    • (1987) The Retina
    • Dowling, J.E.1
  • 3
    • 0346136207 scopus 로고
    • 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.
    • (1995) Isr. J. Chem. , vol.35 , pp. 235-272
    • Nakanishi, K.1    Crouch, R.2
  • 4
    • 0009449979 scopus 로고
    • 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.
    • (1990) Angew. Chem. , vol.102 , pp. 507-526
    • Rando, R.R.1
  • 5
    • 0025298101 scopus 로고
    • 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.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 461-480
  • 6
    • 0002463912 scopus 로고
    • Eds.: M. B. Sporn, A. B. Roberts, D. S. Goodmann, Raven, New York, chap. 9
    • 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.
    • (1994) The Retinoids, Biology, Chemistry and Medicine, 2nd Ed. , pp. 351-395
    • Saari, J.C.1
  • 7
    • 0021225009 scopus 로고
    • Reviews
    • 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.
    • (1984) Tetrahedron , vol.40 , pp. 1931-1969
    • Liu, R.S.H.1    Asato, A.E.2
  • 8
    • 0001980367 scopus 로고
    • Eds.: M. B. Sporn, A. B. Roberts, D.S. Good- mann, Raven, New York, chap. 2
    • 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.
    • (1994) The Retinoids, Biology, Chemistry and Medicine, 2nd Ed. , pp. 5-178
    • Dawson, M.1    Hobbs, P.D.2
  • 9
    • 0030761584 scopus 로고    scopus 로고
    • recent synthesis of (11Z)-retinals
    • 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.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5758-5759
    • Borhan, B.1    Kunz, R.2    Wang, A.Y.3    Nakanishi, K.4    Bojkova, N.5    Yoshihara, K.6
  • 10
    • 0030567869 scopus 로고    scopus 로고
    • and references therein
    • 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.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2049-2052
    • Wada, A.1    Tanaka, Y.2    Fujioka, N.3    Ito, M.4
  • 13
    • 0000929942 scopus 로고
    • 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.
    • (1980) Syn. Commun , vol.10 , pp. 509-515
    • Dugger, R.W.1    Heathcock, C.H.2
  • 15
    • 0028290408 scopus 로고
    • 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.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 757-759
    • Wada, A.1    Hiraishi, S.2    Ito, M.3
  • 17
    • 0347397269 scopus 로고    scopus 로고
    • note
    • 3): δ = 9.0, 13.6,19.3, 27.3, 29.1, 58.8, 139.3, 142.3.
  • 20
    • 0346766757 scopus 로고    scopus 로고
    • note
    • 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.
  • 22
    • 0347397268 scopus 로고    scopus 로고
    • (E)-l-[3-(tert-Butyldimethylsilyl)oxy-l-propenyl]-l,3,2-benzodioxaborole could be used instead of the boronic acid for this reaction
    • (E)-l-[3-(tert-Butyldimethylsilyl)oxy-l-propenyl]-l,3,2-benzodioxaborole could be used instead of the boronic acid for this reaction.
  • 23
    • 0348028032 scopus 로고    scopus 로고
    • note
    • ++H): 271, 2062; found: 271.2068.
  • 25
    • 0346766756 scopus 로고    scopus 로고
    • note
    • +): 268.1826; found: 268.1814.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.