Br[CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1.[Na+].[I-].[C-:21]#[N:22].[K+].[Na].C([O-])(O)=O.[Na+].O>CS(C)=O>[C:21]([CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1)#[N:22]To a vial under an atmosphere of Ar(g) was added 10 (1.23 g, 4.3 mmol), NaI (100 mg), potassium cyanide (0.7 g, 10.6 mmol), and dry DMSO (15 mL). The mixture obtained was heated to 70° C. under an atmosphere of Ar for 12 h. After cooling to room temperature, the reaction mixture was poured into a separatory funnel containing sodium bicarcarbonate aqueous solution (sat. NaHCO3/H2O, 50:50, v:v, 80 mL). The organic fraction was extracted with EtOAc (3×60 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent was then removed in vacuo and the crude product obtained (0.45 g, 86%) was purified by flash column chromatography (EtOAc/hexane, 10:90, v:v, Rf=0.11); as a 2:1 mixture of trans/cis diastereomers. 1H NMR (500 MHz, CDCl3) δ 6.88-6.82 (m, 2 H), 6.74 (dd, J=4.3, 8.5 Hz, 1 H), 4.26 (m, 1 H), 4.09 (m, 0.65 H), 3.90 (m, 0.35 H) 3.79 (s, 3 H), 2.72-2.53 (m, 4 H), 2.22-2.04 (m, 2 H), 1.84-1.6 (m, 4 H).
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