CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@H:24]1[CH2:34][C@@:33]2([CH3:36])[O:35][C@@:25]31[C@@H:37]1[C@@H:29]([N:30]([C:39]4[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([C:47]([F:50])([F:49])[F:48])[CH:40]=4)[C:31](=[O:38])[C@H:32]21)[O:28][CH2:27][CH2:26]3.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[CH3:36][C@:33]12[O:35][C@:25]3([C@@H:37]4[C@@H:29]([N:30]([C:39]5[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([C:47]([F:49])([F:50])[F:48])[CH:40]=5)[C:31](=[O:38])[C@H:32]14)[O:28][CH2:27][CH2:26]3)[C:24](=[O:23])[CH2:34]2Dess-Martin periodinane (12 g, 28.3 mmol) was added to a solution of Example 3 (3.0 g, 7.6 mmol) in THF (20 mL) and CH2Cl2 (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 18 h and CH2Cl2 (50 mL), aq. 15% Na2S2O3 solution (25 mL), and aq. 2M Na2CO3 solution (25 mL) were added. The mixture was stirred for 1 h and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2.9 g (97%) of the Example 5.
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