BULLETIN OF THE
Note
KOREAN CHEMICAL SOCIETY
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at room temperature under nitrogen atmosphere. The mixture
wasstirredfor8 hatroomtemperature. Aftercompletionofthe
reaction, resin was filtered and washed with EtOAc (15 mL).
The filtrate was concentrated in vacuo. Crude residue was
purified by column chromatography (EtOAc/hexane = 1/5)
to yield the compound 15 (16.0 mg, 60%) as pale yellow color
1
viscous oil. Rf 0.51 (EtOAc/hexane = 1/1); H NMR (300
MHz, CDCl3) δ 7.96 (1H, d, J = 16.2 Hz), 7.71 (1H, d,
J = 8.4 Hz), 7.55 (1H, d, J = 16.2 Hz), 7.47 (1H, s), 6.55
(1H, dd J = 8.4, 2.1 Hz), 6.49 (1H, d, J = 2.1 Hz), 6.41 (1H,
s), 6.36 (1H, s), 6.17 (1H, dd J = 17.7, 10.8 Hz), 6.11–5.98
(2H, m), 5.47–5.20 (6H, m), 4.61–4.56 (4H, m), 3.80 (3H,
s), 1.42 (6H, s); 13C NMR (75 MHz, CDCl3) δ 191.1, 162.4,
159.1, 158.8, 157.8, 147.7, 138.1, 132.6, 132.5, 132.4,
127.4, 124.9, 124.2, 123.1, 118.1, 117.4, 116.5, 113.7,
106.0, 100.9, 100.3, 69.2, 68.9, 55.5, 39.8, 27.1.
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(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxy-2-methoxy-
5-(2-methylbut-3-en-2-yl)phenyl)prop-2-en-1-one (Lico-
chalcone G) (7): To a suspension of compound 15 (16.0
mg, 0.04 mmol) and K2CO3 (31.0 mg, 0.22 mmol) in anhy-
drous MeOH (3 mL) was added Pd(PPh3)4 (1.0 mg, 0.002
mmol) at room temperature under nitrogen atmosphere. The
mixture was then stirred at 60 ꢀC for 1.5 h. After completion
of the reaction, 1 N HCl (1 mL) was added and then the mix-
ture was extracted with EtOAc (3 × 20 mL). The combined
organic layer was washed with water (2 × 20 mL), brine
(2 × 20 mL), dried over anhydrous Na2SO4, and concentrated
in vacuo. The crude residue was purified by column chroma-
tography (EtOAc/hexane = 1/3) to yield the compound
7 (12.0 mg, 85%) as yellow color semi solid. Rf = 0.51
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1
(EtOAc/hexane = 1/1); H NMR (300 MHz, CDCl3) δ 8.08
(1H, d, J = 15.0 Hz), 7.84 (1H, d, J = 8.7 Hz), 7.66 (1H, d, J
= 15.0 Hz), 7.48 (1H, s), 6.48–6.42 (2H, br s), 6.45 (1H, d, J
= 8.7 Hz), 6.43 (1H, s), 6.33 (1H, s), 6.21 (1H, dd, J = 17.7,
10.8 Hz), 5.82 (1H, br s), 5.42 (1H, dd, J = 17.7, 1.2 Hz),
5.38 (1H, dd, J = 10.8, 1.2 Hz), 3.92 (3H, s), 1.48 (6H, s);
13C NMR (75 MHz, CDCl3) δ 192.8, 166.4, 162.3, 161.7,
160.0, 158.7, 147.9, 141.5, 132.1, 129.6, 124.7, 118.5, 114.9,
107.7, 103.9, 101.4, 96.3, 56.1, 40.1, 27.3; Electron Impact
Mass Spectrometer (EIMS) m/z 354 (M+), 323 (Base), 137.
HRMS calcd for C21H22O5 M+ 354.1467, found 354.1467.
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Acknowledgments. This research was financially supported
by Priority Research Centers Program through the National
Research Foundation of Korea (NRF) funded by the Ministry
ofEducation, Scienceand Technology (NRF-2009-0094071),
and by the Hallym University Research Fund (HRF-G-
2015-2).
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Bull. Korean Chem. Soc. 2015, Vol. 36, 2784–2787
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