[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@:8]([CH:28]=[CH2:29])([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C1COCC1>[Pd].CO>[CH2:28]([C@@:8]12[CH2:7][CH2:6][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:18]=3[C@H:17]1[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[CH3:29]0.50 g of 13a was dissolved in 25 ml of solvent mixture that consists of THF and methanol (v/v=7/3) and stirred with 0.30 g of palladium (10% on magnesium carbonate) for 3.75 hours at room temperature under hydrogen atmosphere. Then, the reaction solution was filtered on Celite, the filtrate was evaporated to the dry state in a rotary evaporator and the bright foam that was obtained was used without additional purification in the next stage.
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