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HCl (1 n) and then extracted with EtOAc (3ϫ 25 mL). The com-
bined organic phase was washed with brine and dried with anhy-
drous Na2SO4. The crude mixture was purified by preparative thin-
layer chromatography (SiO2, 50 % CH2Cl2 in hexanes, multiple
runs) to provide compounds 4, 5, and 6.
Compound 4: This compound was obtained as a pale yellow oil
1
(6 mg, 5%): H NMR (400 MHz, CDCl3): δ = 7.93–7.85 (m, 2 H,
ArH), 7.56–7.47 (m, 1 H, ArH), 7.44–7.35 (m, 4 H, ArH), 7.34–
7.28 (m, 2 H, ArH), 7.27–7.20 (m, 1 H, ArH), 5.29 (t, J = 6.0 Hz,
1 H, CH), 3.52 (s, 1 H, OH), 3.31 (d, J = 6.0 Hz, 2 H, CH2) ppm.
13C NMR (100 MHz, CDCl3): δ = 200.2 (C), 142.9 (C), 136.6 (C),
133.7 (CH), 128.7 (2ϫ CH), 128.6 (2ϫ CH), 128.2 (2ϫ CH), 127.7
(CH), 125.7 (2ϫ CH), 70.0 (CH), 47.4 (CH2) ppm.
Compound 5: This compound was obtained as a white solid (7 mg,
1
7%): H NMR (400 MHz, CDCl3): δ = 7.65–7.59 (m, 2 H, ArH),
7.33–7.22 (m, 5 H, ArH), 7.21–7.00 (m, 11 H, ArH), 6.99–6.92 (m,
2 H, ArH), 5.61 (d, J = 2.2 Hz, 1 H, CH), 5.22 (d, J = 10.0 Hz, 1
H, CH), 4.32 (dd, J = 10.0, 2.2 Hz, 1 H, CH), 3.89 (dd, J = 10.0,
10.0 Hz, 1 H, CH) ppm. 13C NMR (100 MHz, CDCl3): δ = 202.9
(C), 152.2 (C), 142.7 (C), 138.4 (C), 138.3 (C), 135.0 (C), 132.3
(CH), 128.7 (2ϫ CH), 128.4 (CH), 128.2 (5ϫ CH), 127.8 (2ϫ CH),
127.7 (2ϫCH), 127.5 (2ϫ CH), 127.3 (2ϫ CH), 127.0 (CH), 124.8
(2 ϫ CH), 101.8 (CH), 80.9 (CH), 56.1 (CH), 44.9 (CH) ppm.
HRMS (ESI-TOF): calcd. for C30H24O2Na [M + Na]+ 439.1674;
found 439.1672.
Compound 6:[15] This compound was obtained as a colorless oil
(57 mg, 70 %): 1H NMR (400 MHz, CDCl3): δ = 7.88 (d, J =
7.9 Hz, 4 H, ArH), 7.48 (t, J = 7.4 Hz, 2 H, ArH), 7.42–7.33 (m,
4 H, ArH), 7.27–7.17 (m, 4 H, ArH), 7.16–7.07 (m, 1 H, ArH),
4.00 (quin, J = 7.0 Hz, 1 H, CH), 3.43 (dd, J = 16.7, 7.0 Hz, 2 H,
CH2), 3.29 (dd, J = 16.7, 7.0 Hz, 2 H, CH2) ppm. 13C NMR
(100 MHz, CDCl3): δ = 198.6 (2ϫ C), 143.8 (C), 136.9 (2ϫ C),
133.1 (2ϫ CH), 128.6 (2ϫ CH), 128.5 (4ϫ CH), 128.1 (4ϫ CH),
127.5 (2ϫ CH), 126.7 (CH), 44.9 (2ϫ CH2), 37.2 (CH) ppm.
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Acknowledgments
The authors acknowledge financial support from the Office of the
Higher Education Commission and Mahidol University under the
National Research Universities Initiative, the Thailand Research
Fund through the Royal Golden Jubilee Ph.D. Program (grant
number PHD/0121/2554, grants to T. P. and M. P.), and from the
Center of Excellence for Innovation in Chemistry (PERCH-CIC).
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