[CH2:1]([C:4]1[C:5]([OH:15])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:2]=[CH2:3].[CH3:16][O:17][CH2:18][C:19](=O)[CH3:20].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]2[C:5]=1[O:15][C:19]([CH2:18][O:17][CH3:16])([CH3:20])[CH2:13][C:12]2=[O:14])[CH:2]=[CH2:3]445 mg of 3′-allyl-2′-hydroxy-4′-methoxyacetophenone and 0.57 g of methoxyacetone were dissolved in 10 ml of toluene. Thereafter, 0.19 g of pyrrolidine and 0.19 ml of acetic acid were added to the reaction solution. Thereafter, the reaction solution was heated to reflux using Dean-Stark for 1 hour. Thereafter, the reaction solution was cooled to a room temperature. 1.14 g of methoxyacetone, 0.38 g of pyrrolidine, and 0.38 ml of acetic acid were added to the reaction solution, and the obtained mixture was further heated to reflux overnight. The reaction solution was cooled to a room temperature and then concentrated under a reduced pressure. The residue was diluted with ethyl acetate, and then successively washed with 2 N hydrochloric acid, a 1 N sodium hydroxide aqueous solution, water, and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 194 mg of the subject compound.
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