C([Li])CCC.[CH3:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH3:6][C:7]1[S:8][C:9]([Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21])=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:11]=1Add n-butyllithium (0.46 mL, 0.74 mmol, 1.6 M in tetrahydrofuran) to a solution of 2-methyl-4-phenylthiazole (0.13 g, 0.74 mmol) in tetrahydrofuran (7 mL) cooled to −78° C. under a nitrogen atmosphere. Stir at −78° C. for 45 minutes, add tributyltin chloride (0.2 mL, 0.74 mmol), and stir for 2 hours as the reaction mixture warms to room temperature. Add aqueous ammonium chloride and then partition the mixture between ethyl acetate and water. Extract the aqueous phase with ethyl acetate. Wash the combined organic layers sequentially with water and saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with hexane containing 10% ethyl acetate to provide the desired compound in 68% yield. MS(ES+): m/z=466.1 (M+H)+
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