Tetrahedron Letters

Synthesis of the 7-cis isomer of the natural leukotriene d4

I Ernest, AJ Main, R Menasse

Index: Ernest, I.; Main, A. J.; Menasse, R. Tetrahedron Letters, 1982 , vol. 23, # 2 p. 167 - 170

Full Text: HTML

Citation Number: 37

Abstract

Methyl 5(S), 6(S)-oxido-11-oxo-7-cis-9-trans-undecadienoate 5 was prepared and used for the synthesis of the novel 7-cis-LTD 4 (9) as well as, after isomerization to the all-trans dienal ester 3, for that of the natural leukotrienes. ... 1 H-NMR data on 5 (360 Mc, CDCl 3 , ° in ppm): 1.6-1.9 [2H(3)+2H(4)], 2.41 [2H(2)], 2.93 [H(5), J 5,6 = 2Hz], 3.56 [H(6), J 6,7 = 8Hz], 3.68 [OCH 3 ], 5.59 [H(7), J 7,8 = 11 Hz], 6.21 [H(10), J 9,10 =15, J 10,11 = 8 Hz], 6.46 [H(8), J 8,9 = ...