Journal of Asian Natural Products Research
919
methanol was added over a period of one
and a half hours to the reaction mixture via
a syringe pump, keeping the temperature
between 30 and 358C, and the mixture was
stirred for an additional 1 h. The product
was isolated by extraction with Et2O and
the combined organic layers were washed
with saturated NH4Cl solution and dried
over MgSO4. The solvents were removed
under reduced pressure and the residue
was purified over silica gel (5% Ether/
Hex) to give the title compound 6 (1.28 g,
55%) as colorless oil. 1H NMR (300 MHz,
CDCl3): d 1.41 (m, 4H, H-11, 12), 1.51 (m,
4H, H-10, 13), 1.84 (m, 2H, H-3), 1.94 (t,
1H, J ¼ 2.5 Hz, H-16), 2.19 (dt, 2H,
J ¼ 2.7, 6.9 Hz, H-14), 2.25 (t, 2H,
J ¼ 6.9 Hz, H-9), 2.33 (t, 2H, J ¼ 6.9 Hz,
H-4), 2.45 (t, 2H, J ¼ 7.3 Hz, H-2), 3.67
(s, 3H, OCH3); 13C NMR (125 MHz,
CDCl3): 18.5, 18.8, 19.3, 23.6, 28.3,
28.4, 32.8, 51.7, 65.3, 66.3, 68.3, 76.1,
77.9, 84.7, 173.5. ESI-MS m/z: 259.2
[M þ 1]þ.
(t, J ¼ 6.9 Hz, 2H, H-9), 2.33 (t, J ¼
6.9 Hz, 2H, H-4), 2.44 (t, J ¼ 7.2 Hz, 2H,
H-2), 3.68 (s, 3H, OCH3), 6.16 (dt, J ¼ 1.8,
14.1 Hz, 1H, H-17), 6.56 (d, J ¼ 14.1 Hz,
1H, H-18); 13C NMR (125 MHz, CDCl3):
18.6, 19.1, 19.3, 23.5, 28.1, 28.2, 28.2,
28.3, 32.7, 51.6, 65.2, 66.2, 76.0, 77.3,
77.7, 93.0, 117.0, 118.0. ESI-MS m/z:
363.1, 365.3 [M þ 1]þ.
Acknowledgments
The research work was financially supported by
the Natural Science Foundation of China (Nos
81072572, 81273430, and 21021063), National
Marine ‘863’ Project (Nos 2011AA09070102
and 2013AA092902), the SKLDR/SIMM Pro-
jects (Nos SIMM1203ZZ-03, SIMM1105KF-
04, and SIMM1203KF-12), W.-F.H. thanks
China Postdoctoral Science Foundation Grant
(No. 2012M520956).
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3.2.4. Compound 1
To a round-bottomed flask equipped with
a stirring bar under nitrogen were added
triethylamine (50 ml), Pd(PPh3)4 (0.21 g,
0.18 mmol), CuI (70 mg, 0.36 mmol), a
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