Total synthesis of methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate: A useful intermediate for the synthesis of arachidonic acid analogues

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 771-774

  Han, Luning ^a   Razdan, Raj K ^a  

^a ORGANIX INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACID DERIVATIVE; BROMIDE; METHYL 14 HYDROXY 5,8,11 TETRADECATRIENOATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; REDUCTION;

EID: 0032546104     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10607-4     Document Type: Article

References (19)

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10. 13C NMR 96.7, 83.2, 77.3, 61.8, 60.6, 54.5, 30.0, 25.1, 22.9, 18.8.
11. 6. Hooz, J.; Silani, S. S. H. Can. J. Chem. 1968, 46, 86.
12. 13C NMR 135.4 (4C), 133.5 (2C), 129.5 (2C), 127.6 (4C), 77.5, 76.9, 76.3, 75.3, 62.4, 60.9, 26.7 (3C), 22.9, 22.7, 19.1, 9.6.
13. 2OSitBDP, by treatment with ethylene oxide failed under a variety of conditions presumably due to the acidity of the doubly propargylic protons. For the unstability of the 1,4-diyne unit, see references (a) Gensler, W. J.; Casella, J. Jr. J. Am. Chem. Soc. 1958, 80, 1376.
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17. 11. Labelle, M.; Falgueyret, J. P.; Riendeau, D.; Rokach, J. Tetrahedron 1990, 46, 6301.
18. 1H NMR 7.73-7.61 (m, 4H), 7.46-7.35 (m, 6), 5.47-5.27 (m, 6H), 3.67 (t, 2H, J = 6.8), 3.66 (s, 3H), 2.77-2.71 (m, 4H), 2.39-2.00 (m, 6H), 1.76-1.62 (m, 2H), 1.05 (s, 9H).
19. 3 (M+1) 253.1804. Found 253.1822.