[CH2:1]([Li])CCC.[O:6]([C:13]1[CH:14]=[C:15]([C:19]23[CH2:26][CH2:25][C:22]([CH:27]=O)([CH2:23][CH2:24]2)[O:21][CH2:20]3)[CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[O:6]([C:13]1[CH:14]=[C:15]([C:19]23[CH2:26][CH2:25][C:22]([CH:27]=[CH2:1])([CH2:23][CH2:24]2)[O:21][CH2:20]3)[CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1To a solution of (methyl)triphenylphosphonium bromide (80 mg, 0.224 mmol) in THF (1 mL) at 0° C. was added n-butyllithium (0.140 ml, 0.224 mmol). The reaction mixture was stirred at 0° C. for 30 min. A solution of 4-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octane-1-carbaldehyde (23 mg, 0.075 mmol) in THF (0.5 mL) was then added at 0° C. The reaction was warmed to rt and stirred for 4 h. The reaction was then quenched with saturated aq. NH4Cl, diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (14 mg, 61% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.37-7.29 (m, 3H), 7.14-7.10 (m, 1H), 7.01 (d, J=7.7 Hz, 4H), 6.84 (ddd, J=8.0, 2.4, 0.8 Hz, 1H), 5.89 (dd, J=17.5, 10.9 Hz, 1H), 5.20 (d, J=17.3 Hz, 1H), 5.07 (d, J=10.7 Hz, 1H), 4.08-4.03 (m, 2H), 2.13-1.91 (m, 6H), 1.87-1.80 (m, 2H).
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