W. Jiang et al. / Tetrahedron 67 (2011) 58e68
67
1377, 1162 cmꢁ1
;
1H and 13C NMR data, see Tables 3 and 4; HRMS
1073 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
;
(ESI): calcd for C18H24Br2O4NH4 [MþNH4]þ 480.0380; found
calcd for C17H23Br3O4Na [MþNa]þ 550.9039; found 550.9032,
480.0381, 482.0362, 484.0340 (1:2:1).
552.9013, 554.8999, 556.8973 (1:3:3:1).
20
20
3.3.20. Xestospongiene U (8b). Colorless oil; [
a]
þ5.4 (c 0.5,
3.3.31. Xestospongiene Z6 (11b). Colorless oil. [
a]
þ11.3 (c 0.46,
D
D
MeOH); IR (KBr) nmax 3378, 2924, 2866, 2367, 1738, 1632, 1456,
MeOH); IR (KBr) nmax 3376, 2924, 1732, 1621, 1449, 1380, 1161,
1377, 1162 cmꢁ1
;
1H and 13C NMR data, see Tables 3 and 4; HRMS
1073 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
;
(ESI): calcd for C18H24Br2O4Na [MþNa]þ 484.9934; found 484.9935,
calcd for C17H23Br3O4NH4 [MþNH4]þ 545.9485; found 545.9484,
486.9916, 488.9894 (1:2:1).
547.9463, 549.9441, 551.9420 (1:3:3:1).
20
20
3.3.21. Xestospongiene V (8c). Colorless oil; [
a]
ꢁ5.6 (c 0.5,
3.3.32. Xestospongiene Z7 (11c). Colorless oil. [
a
]
D
ꢁ36.4 (c 0.38,
D
MeOH); IR (KBr) nmax 3416, 3355, 2927, 2367,1736,1668,1450,1372,
MeOH); IR (KBr) nmax 3376, 2924, 1732, 1621, 1449, 1380, 1161,
1073 cmꢁ1. 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
calcd for C17H23Br3O4NH4 [MþNH4]þ 545.9485; found 545.9493,
547.9473, 549.9453, 551.9434 (1:3:3:1).
1160, 1086 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS
;
(ESI): calcd for C18H24Br2O4NH4 [MþNH4]þ 480.0380; found
480.0386, 482.0364, 484.0345 (1:2:1).
20
20
3.3.22. Xestospongiene W (8d). Colorless oil; [
a
]
þ4.8 (c 0.5,
3.3.33. Xestospongiene Z8 (11d). Colorless oil. [
a
]
þ37.7 (c 0.42,
D
D
MeOH); IR (KBr) nmax 3416, 3355, 2927, 2367,1736,1668,1450,1372,
MeOH); IR (KBr) nmax 3376, 2923, 1732, 1621, 1447, 1380, 1162,
1088 cmꢁ1. 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
calcd for C17H23Br3O4Na [MþNa]þ 550.9039; found 550.9047,
552.9027, 554.9007, 556.8986 (1:3:3:1).
1160, 1086 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS
;
(ESI): calcd for C18H24Br2O4Na [MþNa]þ 484.9934; found 484.9939,
486.9918, 488.9898 (1:2:1).
20
20
3.3.23. Xestospongiene X (8e). Colorless oil; [
a
]
D
ꢁ50.8 (c 0.5,
3.3.34. Xestospongiene Z9 (12a). Colorless oil. [
a
]
D
ꢁ21.3 (c 0.5,
MeOH); IR (KBr) nmax 3422, 2958, 2921, 2367, 1733, 1625, 1457, 1377,
MeOH); IR (KBr) nmax 3342, 2923, 2217, 1734, 1440, 1371, 1164, 1060,
1164, 1066 cmꢁ1
;
1H and 13C NMR data, see Tables 3 and 4; HRMS
895 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
.
(ESI): calcd for C18H24Br2O4NH4 [MþNH4]þ 480.0380; found
calcd for C17H22Br3O4 [MþH]þ 526.9063; found 526.9064,
480.0385, 482.0365, 484.0344 (1:2:1).
528.9047, 530.9026, 528.9007 (1:3:3:1).
20
20
3.3.24. Xestospongiene Y (8f). Colorless oil; [
a]
þ49.3 (c 0.5,
3.3.35. Xestospongiene Z10 (12b). Colorless oil. [
a
]
þ20.0 (c 0.5,
D
D
MeOH); IR (KBr) nmax 3422, 2958, 2921, 2367, 1733, 1625, 1457, 1377,
MeOH); IR (KBr) nmax 3342, 2923, 2217, 1734, 1440, 1371, 1164, 1060,
1164, 1066 cmꢁ1
;
1H and 13C NMR data, see Tables 3 and 4; HRMS
895 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4; HRMS (ESI):
.
(ESI): calcd for C18H24Br2O4Na [MþNa]þ 484.9934; found 484.9940,
calcd for C17H21Br3O4NH4 [MþNH4]þ 543.9328; found 543.9337,
486.9919, 488.9897 (1:2:1).
545.9315, 547.9295, 549.9274 (1:3:3:1).
20
3.3.25. Xestospongiene
Z
(9). Colorless oil;
[
a
]
ꢁ2.5 (c 0.5,
3.3.36. Xestospongiene Z11 (13). Colorless oil. IR (KBr) nmax 2954,
D
MeOH); IR (KBr) nmax 3331, 2928, 2855, 2241,1736,1646,1450,1375,
2921, 1737, 1685, 1564, 1378, 1205, 1030, 815 cmꢁ1 1H NMR
.
1217, 808 cmꢁ1
;
1H and 13C NMR data, see Tables 3 and 4; HRMS
(500 MHz, CDCl3): dH 2.46 (2H, t, J¼6.8 Hz, H-2), 2.10 (2H, tt,
J¼6.8, 7.1 Hz, H-3), 3.02 (2H, t, J¼7.1 Hz, H-4), 7.25 (1H, d,
J¼3.4 Hz, H-7), 7.25 (1H, d, J¼3.4 Hz, H-8), 3.10 (2H, t, J¼7.2 Hz,
H-11), 2.50 (2H, td, J¼7.2, 7.6 Hz, H-12), 6.15 (1H, t, J¼7.6 Hz, H-
13), 6.77 (1H, d, J¼7.7 Hz, H-15), 6.47 (1H, d, J¼7.7 Hz, H-16),
3.72 (3H, s, OMe). 13C NMR (125 MHz, CDCl3): dC 175.0 (s, C-1),
32.9 (t, C-2), 18.8 (t, C-3), 37.7 (t, C-4), 189.2 (s, C-5), 153.1 (s, C-
6), 117.1 (d, C-7), 117.1 (d, C-8), 153.3 (s, C-9), 188.6 (s, C-10), 37.2
(t, C-11), 25.1 (t, C-12), 134.2 (d, C-13), 115.1 (s, C-14), 130.9 (d, C-
15), 112.9 (d, C-16), 51.7 (q, OMe); HRMS (ESI): calcd for
C17H18Br2O5Na [MþNa]þ 482.9413; found 482.9413, 484.9400,
486.9388 (1:2:1).
(ESI): calcd for C18H24Br2O5Na [MþNa]þ 500.9883; found 500.9892,
502.9871, 504.9851 (1:2:1).
20
3.3.26. Xestospongiene Z1 (10a). Colorless oil; [
a
]
ꢁ12.4 (c 0.5,
D
MeOH); IR (KBr) nmax 3446, 2928, 2857, 2233, 1734, 1634, 1438,
1373, 1319, 1163, 1061 cmꢁ1; 1H and 13C NMR data, see Tables 3 and
4; HRMS (ESI): calcd for C17H23Br3O3NH4 [MþNH4]þ 529.9536;
found 529.9544, 531.9522, 533.9503, 535.9486 (1:3:3:1).
20
3.3.27. Xestospongiene Z2 (10b). Colorless oil; [
a]
þ11.7 (c 0.5,
D
MeOH); IR (KBr) nmax 3446, 2928, 2857, 2233, 1734, 1634, 1438,
1373, 1319, 1163 cmꢁ1 1H and 13C NMR data, see Tables 3 and 4;
;
20
HRMS (ESI): calcd for C17H23Br3O3Na [MþNa]þ 534.9090; found
3.3.37. Xestospongiene Z12 (14). Colorless oil. [
a
]
D
ꢁ4.0 (c 0.50,
534.9097, 536.9076, 538.9056, 540.9034 (1:3:3:1).
MeOH); IR (KBr) nmax 2921, 2853, 1775, 1741, 1605, 1442, 1257,
1158, 943 cmꢁ1 1H NMR (500 MHz, CDCl3): dH 2.50 (2H, t,
.
20
3.3.28. Xestospongiene Z3 (10c). Colorless oil; [
a
]
ꢁ3.0 (c 0.5,
J¼7.0 Hz, H-2), 1.89 (2H, m, H-3), 5.11 (1H, ddd, J¼1.5, 1.6, 9.0 Hz,
H-4), 6.36 (1H, d, J¼1.6 Hz, H-6), 3.71 (3H, s, OMe). 13C NMR
(125 MHz, CDCl3): dC 172.6 (s, C-1), 28.5 (t, C-2), 27.5 (t, C-3), 84.0
(d, C-4), 150.1 (s, C-5), 122.5 (d, C-6), 169.8 (s, C-7), 52.0 (q, OMe);
HRMS (ESI): calcd for C8H979BrO4Na [MþNa]þ 270.9576; found
270.9576, 272.9555 (1:1).
D
MeOH); IR (KBr) nmax 3422, 2938, 2857, 2232, 1735, 1647, 1594,
1436, 1373, 1318, 1224, 1165 cmꢁ1; 1H and 13C NMR data, see Tables
3
and 4; HRMS (ESI): calcd for C17H23Br3O3NH4 [MþNH4]þ
529.9536; found 529.9543, 531.9523, 533.9502, 535.9482 (1:3:3:1).
20
3.3.29. Xestospongiene Z4 (10d). Colorless oil; [
a
]
þ3.2 (c 0.5,
D
MeOH); IR (KBr) nmax 3422, 2938, 2857, 2232, 1735, 1647, 1594,
1436, 1373, 1318, 1224, 1165 cmꢁ1; 1H and 13C NMR data, see Tables
3 and 4; HRMS (ESI): calcd for C17H23Br3O3Na [MþNa]þ 534.9090;
found 534.9100, 536.9077, 538.9056, 540.9033 (1:3:3:1).
3.3.38. Xestospongiene Z13 (15). Colorless oil. IR (KBr) nmax 2956,
2924, 1611, 1453, 1380, 1116, 817 cmꢁ1. 1H NMR (500 MHz, CDCl3):
dH 6.20 (1H, d, J¼16.0 Hz, H-8), 6.77 (1H, dt, J¼2.9, 16.0 Hz, H-7),
2.49 (2H, m, H-4), 1.93 (2H, m, H-3), 2.49 (2H, m, H-2), 3.77 (3H, s,
OMe-9), and 3.71 (3H, s, OMe-1). 13C NMR (125 MHz, CDCl3): dC
166.5 (s, C-9), 129.3 (d, C-8), 126.0 (d, C-7), 77.4 (s, C-6), 99.2 (s, C-5),
19.2 (t, C-4), 23.5 (t, C-3), 32.8 (t, C-2),173.4 (s, C-1), 51.7 (q, OMe-9),
20
3.3.30. Xestospongiene Z5 (11a). Colorless oil. [
a
]
ꢁ12.8 (c 0.7,
D
MeOH); IR (KBr) nmax 3376, 2924, 1732, 1621, 1449, 1380, 1161,