[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17](CO)([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O-])(O)=[O:25].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:19][CH2:18][C:17]([CH:16]=[O:15])([CH2:20][CH2:21]2)[O:25][CH2:24]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a mixture of (4-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-1-yl)methanol (5A; 182 mg, 0.586 mmol) and NaHCO3 (59 mg, 0.704 mmol) in CH2Cl2 (5 mL) at 0° C. was added Dess-Martin periodinane (298 mg, 0.70 mmol). The solution was warmed to rt and stirred for 1 h. The reaction was diluted with EtOAc, washed successively with sat'd aq NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (0 to 100% EtOAc:hexanes) to afford the title compound (123 mg, 68% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 9.65 (s, 1H), 7.41-7.28 (m, 3H), 7.12-7.16 (m, 1H), 7.06-6.89 (m, 4H), 6.88 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 4.12-4.09 (m, 2H), 2.17-1.90 (m, 8H).
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