C(=O)CCCCCCCCC/C=C\CCCC.CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH:38]([OH:49])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].CCN(CC)CC>>[CH3:48][CH2:47][CH2:46][CH2:45][CH2:44]/[CH:43]=[CH:42]\[CH2:41][CH2:40][CH2:39][C:38](=[O:49])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28]According to the procedure for compound 6, DMSO (0.080 mL, 1.1 mmol), oxalyl chloride (0.060 mL, 0.67 mmol), alcohol 19 (0.19 g, 0.61 mmol), and Et3N (0.42 mL, 3.1 mmol) were reacted to yield 20 (0.17 g, 91% yield, 88% Z as determined by quantitative 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.39 (1H, m), 5.31 (1H, m), 2.39 (2H, t, J=7.5 Hz), 2.38 (2H, t, J=7.6 Hz), 2.04 (2H, m), 1.99 (2H, m), 1.63 (2H, m), 1.56 (2H, m), 1.20-1.37 (20H, m), 0.88 (6H, m); 13C NMR (CDCl3): δ 211.4, 131.0, 128.7, 42.9, 42.1, 31.9, 31.5, 29.6, 29.5, 29.4 (2C), 29.3 (2C), 23.9, 22.7, 22.6, 14.1 (2C); HRMS (FAB): 309.3148, [C21H40O+H]+ requires 309.3157.
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