## 2 Materials and Methods
### Chemistry
#### 2.1.2 Experimental Section  
_(E)-3-(2-(Benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyyl)prop-2-en-1-one_ (6). To a solution of 4,6-dimethoxy-2-hydroxybenzophenone 4 (700 mg, 3.57 mmol) and 2-(benzyloxy)benzaldehyde 5 (1100 mg, 5.35 mmol) in ethyl alcohol (11 mL), KOH (400 mg, 7.14 mmol) was added at room temperature. After stirring at the same temperature for 48 h, the reaction mixture was concentrated in vacuo. The reaction mixture was quenched with 1N aqueous solution of hydrochloric acid and extracted with EtOAc (ethyl acetate). The combined organic layer was washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the concentrated residue by flash column chromatography (EtOAc/_n_-Hexane = 1 : 40 to 1 : 10) afforded 1500 mg (75%) of chalcone 6 as a yellow powder. m.p. : 114-115 \({}^{\circ}\)C; R\({}_{f}\) = 0.25 (EtOAc : \(n\)-Hexane = 1 : 10); \({}^{1}\)H NMR (800 MHz, CDCl\({}_{3}\)) 8 14.37 (s, 1H), 8.17 (d, 1H, \(J\) = 15.8 Hz), 8.02 (d, 1H, \(J\) = 15.7 Hz), 7.62 (dd, 1H, \(J\) = 1.5, 7.7 Hz), 7.46 (d, 2H, \(J\) =7.6 Hz), 7.39-7.37 (m, 2H), 7.33-7.30 (m, 2H),  
Figure 1: The structures of oleracones D (**1**), F (**2**), and E (**3**). 7.00 (t, 1H, \(J\) = 7.5 Hz), 6.87 (d, 1H, \(J\) = 8.2 Hz), 6.10 (d, 1H, \(J\) = 2.3 Hz), 5.91 (d, 1H, \(J\) = 2.3 Hz), 5.20 (s, 2H), 3.83 (s, 3H), 3.72 (s, 3H); \({}^{13}\)C NMR (200 MHz, CDCl\({}_{3}\)) 8 193.3, 168.4, 166.2, 162.6, 157.9, 138.1, 136.9, 131.4, 129.5, 128.8, 128.5, 128.1, 127.3, 125.1, 121.2, 112.9, 106.6, 93.8, 93.8, 91.3, 70.5, 55.7, 55.7; IR (thin film, neat) \(\
u_{\rm max}\) 1620, 1595, 1553, 1452, 1344, 1213, 1107, 984, 816, 760 cm\({}^{-1}\); LR-MS (Low-Resolution Mass Spectroscopy) (FAB+) _m/z_ 391 (M + H\({}^{+}\)); HR-MS (High-Resolution Mass Spectroscopy) (FAB+) calculated for C\({}_{24}\)H\({}_{23}\)O\({}_{5}\) (M + H\({}^{+}\)) 391.1545; observed 391.1541. _Oleracone E._ (3). To a solution of chalcone 6 (500 mg, 1.28 mmol) in ethyl alcohol (10 mL), catalytic amount of 5% activated palladium on carbon was added at room temperature. After stirring for 48 h under H\({}_{2}\) atmosphere, the reaction mixture was filtered through a pad of Celite and concentrated in vacuo. Purification of the concentrated residue by flash column chromatography (EtOAc: \(n\)-Hexane = 1 : 10 to 1 : 3) afforded 340 mg (88%) of olerone E (3) as a yellowish powder. The spectral data of 3 were consistent with previous data (Table S1). m.p. : 137-138 \({}^{\circ}\)C; R\({}_{\rm f}\) = 0.20 (EtOAc/\(n\)-Hexane = 1:5); \({}^{1}\)H NMR (500 MHz, DMSO-d\({}_{6}\)) 8 13.63 (brs, 1H), 9.30 (brs, 1H), 7.06 (dd, 1H, \(J\) = 1.5, 7.4 Hz), 6.99 (brtd, 1H, \(J\) = 1.6, 7.7 Hz), 6.77(dd, 1H, \(J\) = 1.0, 8.0 Hz), 6.70 (td, 1H, \(J\) = 1.0, 7.4 Hz), 6.11 (d, 1H, \(J\) = 2.4 Hz), 6.09 (d, 1H, \(J\) = 2.4 Hz), 3.82 (s, 3H), 3.80 (s, 3H), 3.20 (brt, 2H, \(J\) = 7.7 Hz), 2.81 (brt, 2H, \(J\) = 7.7 Hz); \({}^{13}\)C NMR (200 MHz, DMSO-d\({}_{6}\)) 8 205.4, 166.1, 166.0, 162.9, 155.5, 130.3, 127.7, 127.5, 119.5, 115.3, 106.0, 94.2, 91.2, 56.4, 56.1, 43.9, 25.5; IR (thin film, neat) \(\
u_{\rm max}\) 1618, 1578, 1489, 1462, 1418, 1362, 1204, 1109, 999, 829, 758 cm\({}^{-1}\); LR-MS (FAB+) _m/z_ 303 (M + H\({}^{+}\)); HR-MS (FAB+) calculated for C\({}_{17}\)H\({}_{19}\)O\({}_{5}\) (M + H\({}^{+}\)) 303.1232; observed 303.1226. _Oleracone F._ (2). _N,N_-Dmethylformamide dimethyl acetal (0.053 mL, 0.40 mmol) was added to a solution of olerone E (3) (100 mg, 0.33 mmol) in toluene (5.5 mL) at room temperature. The reaction mixture was refluxed for 2 h, and then cooled to room temperature. The reaction mixture was concentrated in vacuo. Purification of the concentrated residue by flash column chromatography (EtOAc: \(n\)-Hexane = 1 : 2) afforded 93 mg (90%) of olerone F (2) as a yellow powder. The spectral data of 2 were consistent with previous data (Table S2). m.p.