Journal of Asian Natural Products Research
1185
3.3.4 Compound 9
3.3.7 Compound 12
Pale yellow solid (60.8%); m.p. 227–
2298C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.44 (s, 1H, Ar-H), 8.30 (d, 1H,
J ¼ 8.4 Hz, Ar-H), 7.99 (d, 1H, J ¼ 8.4 Hz,
Ar-H), 7.91 (t, 1H, J ¼ 8.4 Hz, Ar-H), 7.72
(t, 2H, J ¼ 8.4 Hz, Ar-H), 7.57 (d, 1H,
J ¼ 9.3 Hz, Ar-H), 7.38 (t, 2H, J ¼ 8.4 Hz,
Ar-H), 7.22 (d, 1H, J ¼ 2.4 Hz, Ar-H), 7.02
(m, 2H, Ar-H), 5.80–5.49 (m, 2H, 17-H),
5.24 (d, 2H, J ¼ 3.0 Hz, 5-H), 4.91, 4.83 (d,
2H, J ¼ 16.2 Hz, 20-OZCOCH2ZOZ),
4.36, 3.14 (dd, 2H, J ¼ 13.8Hz, 21-H),
2.32, 1.97 (m, 2H, 19-CH2), 1.13 (t, 3H,
J ¼ 7.8 Hz, 18-CH3); HR-ESI-MS: m/z
Pale yellow solid (66.8%); m.p. 246–
2488C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.43 (s, 1H, Ar-H), 8.24 (d, 1H,
J ¼ 8.4 Hz, Ar-H), 7.95 (d, 1H, J ¼ 8.4 Hz,
Ar-H), 7.85 (t, 1H, J ¼ 8.4 Hz, Ar-H), 7.77
(d, 2H, J ¼ 8.4 Hz, Ar-H), 7.69 (t, 1H,
J ¼ 7.8 Hz, Ar-H), 7.44 (t, 2H, J ¼ 6.3 Hz,
Ar-H), 7.36 (s, 1H, Ar-H), 7.20 (t, 1H,
J ¼ 7.8 Hz, Ar-H), 7.07 (t, 1H, J ¼ 8.4 Hz,
Ar-H), 6.97 (d, 2H, J ¼ 8.4 Hz, Ar-H), 5.85,
5.49 (dd, 2H, J ¼ 15.6Hz, 17-H), 5.28
(d, 2H, J ¼ 6.9 Hz, 5-H), 4.81 (dd, 2H,
J ¼ 16.2Hz, 20-OZCOCH2O), 4.33, 3.14
(d, 2H, J ¼ 13.2 Hz, 21-H), 2.27, 1.95
(m, 2H, 19-CH2), 1.11 (t, 3H, J ¼ 6.9 Hz,
18-CH3); HR-ESI-MS: m/z 619.1865
[M þ H]þ (calcd for C35H28N3O8,
619.1832).
625.0961
[M þ H]þ
(calcd
for
C33H26BrN2O6, 625.0974).
3.3.5 Compound 10
Pale yellow solid (48.0%); m.p. 162–
1648C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.43 (s, 1H, Ar-H), 8.24 (d, 1H,
J ¼ 8.7 Hz, Ar-H), 7.95 (d, 1H, J ¼ 8.7 Hz,
Ar-H), 7.86 (t, 1H, J ¼ 8.7 Hz, Ar-H), 7.69
(t, 1H, J ¼ 8.7 Hz, Ar-H), 7.33 (s, 1H,
Ar-H), 7.17 (m, 3H, Ar-H), 5.84–5.48 (dd,
2H, J ¼ 15.3Hz, 17-H), 5.28 (s, 2H, 5-H),
4.83 (d, 2H, J ¼ 7.8 Hz, 21-H), 4.40, 3.07
(dd, 1H, J ¼ 13.2 Hz, 20-OZCOCH2-
ZOZ), 2.32, 1.96 (m, 2H, 19-CH2), 1.13
(t, 3H, J ¼ 6.9 Hz, 18-CH3); HR-ESI-MS:
m/z 583.1481 [M þ H]þ (calcd for
C30H23F4N2O6, 583.1414).
3.3.8 Compound 13
Pale yellow solid (57.4%); m.p. 139–
1418C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.38 (s, 1H, Ar-H), 8.23 (d, 1H,
J ¼ 8.4 Hz, Ar-H), 7.93 (d, 1H, J ¼ 8.4 Hz,
Ar-H), 7.84 (t, 1H, J ¼ 8.4 Hz, Ar-H), 7.67
(t, 1H, J ¼ 8.4 Hz, Ar-H), 7.27 (s, 1H,
Ar-H), 6.79 (d, 2H, J ¼ 8.4 Hz, Ar-H), 6.72
(d, 2H, J ¼ 6.3 Hz, Ar-H), 5.82, 5.46 (dd,
2H, J ¼ 16.5Hz, 17-H), 5.24 (s, 2H, 5-H),
4.67 (d, 2H, J ¼ 2.4 Hz, 20-OZCOCH2-
OZ), 4.38, 3.08 (dd, 2H, J ¼ 13.8Hz, 21-
H), 3.52(s, 3H, 40-OCH3),2.28, 1.93(m, 2H,
19-CH2), 1.13 (t, 3H, J ¼ 7.8 Hz, 18-CH3);
HR-ESI-MS: m/z 527.1814 [M þ H]þ
(calcd for C30H27N2O7, 527.1818).
3.3.6 Compound 11
Pale yellow solid (60.5%); m.p. 190–
1928C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.46 (1H, s, Ar-H), 8.26 (d, 1H,
J ¼ 8.7 Hz, Ar-H), 7.89 (d, 1H, J ¼ 7.8 Hz,
Ar-H), 7.81 (t, 1H, J ¼ 8.7 Hz, Ar-H), 7.72
(t, 1H, J ¼ 7.8 Hz, Ar-H), 7.30 (s, 1H, Ar-
H), 7.13 (m, 3H, Ar-H), 5.73, 5.54 (d, 2H,
J ¼ 15.3Hz, 17-H), 5.29 (s, 2H, 5-H), 4.86
(m, 2H, 20-OZCOCH2ZO), 4.22, 3.23 (dd,
2H, J ¼ 13.8Hz, 21-H), 2.34, 2.03 (m, 2H,
19-CH2), 1.13 (t, 3H, J ¼ 7.8 Hz, 18-CH3);
HR-ESI-MS: m/z 610.1424 [M þ H]þ
(calcd for C30H23F3N3O8, 610.1437).
3.3.9 Compound 14
Pale yellow solid (70.5%); m.p. 163–
1658C; 1H NMR (300 MHz, CDCl3, d
ppm): 8.41 (s, 1H, Ar-H), 8.23 (d, 1H,
J ¼ 8.4 Hz, Ar-H), 7.95 (d, 1H, J ¼ 8.7 Hz,
Ar-H), 7.86 (t, 1H, J ¼ 8.4 Hz, Ar-H), 7.69
(t, 1H, J ¼ 8.7 Hz, Ar-H), 7.03 (d, 2H,
J ¼ 9.3 Hz, Ar-H), 7.26 (s, 1H, Ar-H), 6.89
(d, 2H, J ¼ 9.3 Hz, Ar-H), 5.81, 5.49 (dd,
2H, J ¼ 16.5Hz, 17-H), 5.27 (s, 2H, 5-H),