Stereoselective synthesis of 10,11-dihydro-leukotriene B4 and related metabolites

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6337-6340

  Kobayashi, Yuichi ^a   Nakayama, Yuji ^a   Biju Kumar, G ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Boron and compounds; Coupling reactions; Dienes; Nickel and compounds

Indexed keywords

10,11 DIHYDROLEUKOTRIENE; BORIC ACID; BROMIDE; LEUKOTRIENE; LIPOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; ESTERIFICATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032572854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01346-X     Document Type: Article

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28. 3) of 7a: δ 0.01, 0.04, 0.049, 0.052 (4s, 12 H), 0.87 (s, 9 H), 0.88 (t, J = 7 Hz, 3 H), 0.89 (s, 9 H), 1.2-1.8 (m, 12 H), 2.01 (q, J = 7 Hz, 2 H), 2.07-2.25 (m, 4 H), 2.31 (t, J = 7 Hz, 2 H), 3.66 (s, 3 H), 3.62-3.74 (m, 1 H), 4.52 (dt, J = 9, 6 Hz, 1 H), 5.23 (dd, J = 11, 9 Hz, 1 H), 5.32-5.50 (m, 2 H), 5.68 (dt, J = 15, 7 Hz, 1 H), 5.88 (t, J = 11 Hz, 1 H), 6.22 (dd, J = 15, 11 Hz, 1 H).
29. 2O, reflux, 18 h) gave the acid of 7a only in lower yields of <30%.
30. 3) of 7b: δ 0.04 (s, 12 H), 0.87 (s, 9 H), 0.88 (t, J = 7 Hz, 3 H), 0.89 (s, 9 H), 1.2-1.8 (m, 20 H), 2.04-2.19 (m, 2 H), 2.31 (t, J = 7 Hz, 2 H), 3.66 (s, 3 H), 3.60-3.69 (m, 1 H), 4.55 (dt, J = 9, 6 Hz, 1 H), 5.23 (dd, J = 11, 9 Hz, 1 H), 5.68 (dt, J = 15, 7 Hz, 1 H), 5.89 (t, J = 11 Hz, 1 H), 6.22 (dd, J = 15, 11 Hz, 1 H).