[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH2:13][CH2:14][N:15]=[C:8]1[CH2:7][CH2:6]2.[CH:16]([O:19]C)(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:16]=[O:19])[N:9]1[CH2:13][CH2:14][N:15]=[C:8]1[CH2:7][CH2:6]2To a stirred solution of Compound 14 (63 mg, 0.31 mmol) in CH2Cl2 (5 ml) was added TiCl4 (0.17 ml, 1.6 mmol) at 0° C. After the reaction mixture was stirred for 10 minutes, Cl2CHOMe (0.14 ml, 1.6 mmol) was added at 0° C., and stirred for 3 h. The mixture was quenched by the addition of water, basified with NaOH aq., and extracted with CH2Cl2. The combined CH2Cl2 extracts were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography to give Compound 15 (25 mg, 35%) as a slight yellow solid.
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