[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Cl[CH2:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:16][CH:15]=1.[I-].[K+]>C1COCC1>[O:4]=[C:3]([CH3:5])[CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:26][CH:27]=1)[C:1]([O:7][CH2:8][CH3:9])=[O:6]Ethyl acetoacetate (11.7 ml) was added to a stirred suspension of sodium hydride (60% disp. in oil, 3.8 g) in THF (200 ml) at 0° C. under nitrogen. After 1 h, a solution of 2-(4-(chloromethyl)benzyloxy)tetrahydro-2H-pyran (22.2 g) in THF (50 ml) was added, the mixture warmed to rt, then potassium iodide (16 g) added and heated under reflux for 48 h. The mixture was partitioned between water and ether, the organics separated, washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 20% EtOAc in isohexane to afford the subtitle compound, 15.66 g.
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