C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:21][CH:22]1[C:23]([O:65]C(OCC)C)([CH3:64])[CH2:24][CH2:25][CH:26]([O:58]C(OCC)C)[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([O:48]C(OCC)C)[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[NH2:19]>CO>[C:18]([O:21][CH:22]1[C:23]([OH:65])([CH3:64])[CH2:24][CH2:25][CH:26]([OH:58])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([OH:48])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[NH2:19]Pyridinium p-toluenesulfonate (1.2 mg, 4.8 μmol) was added to a solution of (8E,12E,14E)-7-carbamoyloxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (3.6 mg, 4.77 μmol) in methanol (1 mL), followed by stirring at room temperature for 3 hours. The reaction mixture was evaporated, ethyl acetate, water and a saturated sodium bicarbonate aqueous solution were added to the resulting residue, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; methanol-dichloromethane, 1:29) to give the title compound (1.9 mg, 74%) as a colorless oil.
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