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Volumn 38, Issue 35, 1997, Pages 6209-6212

Synthesis of fluorinated analogs of polyunsaturated fatty acid metabolites (4 HNE, 13 HODE)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYNONENAL; CORIOLIC ACID; POLYUNSATURATED FATTY ACID;

EID: 0343742611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01400-7     Document Type: Article
Times cited : (14)

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    • The interesting studies from Buists' group on the use of fluorine substituent effects in the fatty acid biosynthetic problems have also to be noticed. See for instance: Buist, P.H.; Findlay, J.M. Tetrahedron Lett., 1984, 25, 1433-1436. Buist, P.H.; Pon, R.A. J. Org. Chem., 1990, 55, 6240-6241. Buist, P.H.; Behrouzian, B.; Alexopoulos, K.A.; Dawson, B.; Black, B. Chem. Commun., 1996, 2671-2672.
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    • Guindon, Y.; Delorme, D. Can. J. Chem., 1987, 65, 1438-1440. Hanzawa, Y.; Kawagoe, K.I.; Inazawa, K.; Kobayashi, Y. Tetrahedron Lett., 1988, 29, 5665-5666. Tanaka, Y.; Klauck, T.M.; Jubiz, W.; Taguchi, T.; Hanzawa, Y.; Igarashi A.; Inazawa, K.; Kobayashi, Y.; Briggs, R.G. Arch. Biochem. Biophys., 1988, 263, 178-190. Garcia, M.; Durand, T.; Girard, J.P.; Rossi, J.C.; Serkov, I.; Kuklev, D., Bezuglov, V. Tetrahedron Lett., 1995, 36, 6437-6438.
    • (1988) Arch. Biochem. Biophys. , vol.263 , pp. 178-190
    • Tanaka, Y.1    Klauck, T.M.2    Jubiz, W.3    Taguchi, T.4    Hanzawa, Y.5    Igarashi, A.6    Inazawa, K.7    Kobayashi, Y.8    Briggs, R.G.9
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    • Guindon, Y.; Delorme, D. Can. J. Chem., 1987, 65, 1438-1440. Hanzawa, Y.; Kawagoe, K.I.; Inazawa, K.; Kobayashi, Y. Tetrahedron Lett., 1988, 29, 5665-5666. Tanaka, Y.; Klauck, T.M.; Jubiz, W.; Taguchi, T.; Hanzawa, Y.; Igarashi A.; Inazawa, K.; Kobayashi, Y.; Briggs, R.G. Arch. Biochem. Biophys., 1988, 263, 178-190. Garcia, M.; Durand, T.; Girard, J.P.; Rossi, J.C.; Serkov, I.; Kuklev, D., Bezuglov, V. Tetrahedron Lett., 1995, 36, 6437-6438.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6437-6438
    • Garcia, M.1    Durand, T.2    Girard, J.P.3    Rossi, J.C.4    Serkov, I.5    Kuklev, D.6    Bezuglov, V.7
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    • For the first example with DAST see: Middleton, W.J. J. Org. Chem., 1975, 40, 574-578. All the corresponding data are discussed in a recent review: Grée, R.L.; Lellouche, J.P. EPC Synthesis of Fluoro- Organic Compounds: Stereochemical Challenges and Biomedicinal Targets, Soloshonok, V.A. Ed., John Wiley and Sons, Chichester, UK, in print, 1997.
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    • Middleton, W.J.1
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    • note
    • However, it should be pointed out that both for the TLC analysis and the flash chromatographic purification of these compounds, the silica gel must be pretreated with eluents containing triethylamine.
  • 49
    • 0343578723 scopus 로고    scopus 로고
    • note
    • 3), 93.6 (J= 165.3, C-9), 127.5 (J= 12.0, C-7), 128.4 (J= 2.7, C-6), 131.4 (J= 18.2, C-8), 132.5 (J= 3.3, C-5), 173.9 (C-1). IR (neat): 1735.


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