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YI ET AL.
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Compound 5b
Compound 5e
Compound 5b was prepared according to the general procedure from
compound 4b and iodomethane. The crude product was purified over
silica gel column chromatography to give as a white solid (0.472 g,
82%). IR (KBr): 3447, 2984, 2945, 1731, 1458, 1409, 1238, 1121,
1023 cm−1. 1H NMR (400 MHz, d-DMSO) δ 6.20–6.06 (m, 1H), 5.63 (d,
J = 8.0 Hz, 1H), 5.11 (s, 1H), 5.08 (d, J = 2.8 Hz, 1H), 4.63 (d, J = 5.8 Hz,
1H), 4.44 (dd, J = 48.3, 17.6 Hz, 2H), 3.51 (dd, J = 23.9, 14.3 Hz, 5H),
3.10 (s, 3H), 2.48 (s, 1H), 2.20 (d, J = 9.3 Hz, 2H), 2.14–1.99 (m, 2H),
1.67 (s, 2H), 1.48 (d, J = 16.0 Hz, 2H), 1.39 (s, 4H), 1.29 (d, J = 13.0 Hz,
2H), 1.23 (dd, J = 11.7, 7.0 Hz, 6H), 1.10 (s, 4H), 0.86 (d, J = 6.8 Hz, 3H),
0.66 (d, J = 6.9 Hz, 3H). 13C NMR (101 MHz, d-DMSO) δ 217.40,
164.25, 141.55, 115.78, 72.89, 71.76, 58.20, 57.54, 57.39, 47.97,
45.38, 44.85, 43.81, 41.99, 37.13, 36.62, 34.44, 30.57, 29.40, 27.02,
24.92, 16.54, 14.92, 12.10, 8.15. HRMS (ESI) calcd. [M]+ for
Compound 5e was prepared according to the general procedure
from compound 4e and iodomethane. The crude product was
purified over silica gel column chromatography to give yellow solid
(0.423 g, 72%). IR (KBr): 3462, 3393, 3023, 3001, 2985, 2974,
2943, 2874, 1734, 1474, 1458, 1227, 1197, 1121, 1021, 986, 938,
911 cm−1 1H NMR (400 MHz, d-DMSO) δ 6.22–6.01 (m, 1H), 5.63
.
(d, J = 8.0 Hz, 1H), 5.09 (dd, J = 14.5, 1.9 Hz, 2H), 4.64 (d,
J = 17.1 Hz, 2H), 4.45 (d, J = 17.3 Hz, 1H), 3.70–3.61 (m, 1H),
3.54 (d, J = 4.1 Hz, 2H), 3.45 (s, 2H), 3.21 (s, 3H), 2.47 (s, 1H), 2.26–
2.01 (m, 4H), 1.91–1.76 (m, 4H), 1.66 (s, 2H), 1.53 (s, 3H), 1.48 (d,
J = 11.6 Hz, 1H), 1.41 (d, J = 9.7 Hz, 1H), 1.39 (s, 3H), 1.30 (t,
J = 10.4 Hz, 2H), 1.09 (s, 4H), 0.86 (d, J = 6.8 Hz, 3H), 0.66 (d,
J = 6.9 Hz, 3H). 13C NMR (101 MHz, d-DMSO) δ 217.42, 164.19,
141.49, 115.81, 72.88, 71.71, 61.60, 60.28, 57.59, 48.59, 45.39,
44.93, 43.58, 42.02, 37.23, 36.65, 34.45, 30.59, 29.54, 27.00,
24.95, 21.04, 19.58, 16.50, 14.95, 12.13. HRMS (ESI) calcd. [M]+
for C28H46NO4 460.3421. Found 460.3428.
C27H46NO4 448.3421. Found 448.3426.
Compound 5c
Compound 5c was prepared according to the general procedure from
compound 4c and iodomethane. The crude product was purified over
silica gel column chromatography to give as a white solid (0.368 g,
64%). IR (KBr) 3530, 2949, 1742, 1717, 1458, 1231, 1209, 1126,
1013 cm−1. 1H NMR (400 MHz, d-DMSO) δ 6.12 (dd, J = 18.1, 10.9 Hz,
1H), 5.63 (d, J = 8.0 Hz, 1H), 5.20–4.96 (m, 2H), 4.74 (dt, J = 21.6,
10.9 Hz, 1H), 4.59 (d, J = 17.0 Hz, 2H), 4.08–3.82 (m, 4H), 3.68 (dd,
J = 18.8, 13.4 Hz, 1H), 3.56 (dd, J = 29.4, 15.8 Hz, 3H), 3.45 (d,
J = 5.3 Hz, 1H), 3.33 (s, 3H), 2.48 (s, 1H), 2.27–2.12 (m, 2H), 2.12–2.06
(m, 1H), 2.06–2.00 (m, 1H), 1.73–1.59 (m, 2H), 1.50 (d, J = 15.9 Hz, 2H),
1.48–1.40 (m, 1H), 1.36 (s, 3H), 1.33–1.26 (m, 2H), 1.12–0.98 (m, 4H),
0.85 (d, J = 6.8 Hz, 3H), 0.67 (d, J = 6.9 Hz, 3H). 13C NMR (101 MHz,
d-DMSO) δ 217.41, 163.97, 141.48, 115.86, 72.87, 71.93, 61.78,
60.51, 60.10, 57.53, 47.53, 45.39, 44.93, 43.55, 42.02, 37.21, 36.63,
34.44, 30.55, 29.52, 27.01, 24.94, 16.56, 14.91, 12.12. HRMS (ESI)
calcd. [M]+ for C27H44NO4 446.3215. Found 446.3221.
Compound 5f
Compound 5f was prepared according to the general procedure from
compound 4f and iodomethane. The crude product was purified over
silica gel column chromatography to give yellow solid (0.361 g, 59%). IR
(KBr): 3422, 2926, 1730, 1458, 1240, 1222, 1022, 912 cm−1. 1H NMR
(400 MHz, d-DMSO) δ 6.11 (dd, J = 17.3, 11.2 Hz, 1H), 5.62 (d,
J = 6.3 Hz, 1H), 5.47 (s, 1H), 5.09 (d, J = 12.7 Hz, 2H), 4.62 (s, 2H), 4.47
(d, J = 17.6 Hz, 1H), 4.10–3.97 (m, 1H), 3.53 (s, 3H), 3.45 (s, 2H), 3.35 (s,
2H), 3.24 (d, J = 7.4 Hz, 2H), 3.16 (d, J = 4.1 Hz, 1H), 2.47 (s, 1H),
2.28–1.94 (m, 5H), 1.80 (s, 2H), 1.66 (s, 2H), 1.49 (s, 3H), 1.37 (s, 3H),
1.29 (s, 3H), 1.08 (s, 4H), 0.85 (d, J = 5.4 Hz, 3H), 0.65 (d, J = 6.9 Hz, 3H).
13C NMR (101 MHz, d-DMSO) δ 217.41, 164.11, 141.48, 115.83,
72.87, 71.77, 64.58, 63.86, 61.59, 60.98, 57.59, 51.04, 49.72, 49.07,
45.38, 44.94, 43.58, 41.98, 37.24, 36.65, 34.45, 30.60, 29.56, 27.00,
24.95, 17.00, 16.52, 14.95, 12.14. HRMS (ESI) calcd. [M]+ for
C29H48NO5 490.3527. Found 490.3529.
Compound 5d
Compound 5d was prepared according to the general procedure from
compound 4d and iodomethane. The crude product was purified over
silica gel column chromatography to give as a yellow solid (0.326 g,
55%). IR (KBr): 3630, 3316, 2985, 2960, 2920, 2862, 1732, 1458,
1422, 1407, 1259, 1226, 1171, 1155, 1124, 1091, 1053, 1016, 941,
913 cm−1. 1H NMR (400 MHz, d-DMSO) δ 6.13 (dd, J = 17.7, 11.3 Hz,
1H), 5.64 (dd, J = 10.3, 5.8 Hz, 2H), 5.16–5.03 (m, 2H), 4.66–4.61 (m,
1H), 4.60–4.46 (m, 3H), 3.90–3.80 (m, 1H), 3.72 (dd, J = 12.4, 5.1 Hz,
1H), 3.60 (d, J = 12.1 Hz, 2H), 3.49–3.37 (m, 2H), 3.32 (s, 1H), 2.47 (s,
2H), 2.24–2.01 (m, 5H), 1.64 (d, J = 13.3 Hz, 2H), 1.49 (s, 2H), 1.45 (s,
1H), 1.37 (s, 3H), 1.30 (t, J = 8.9 Hz, 2H), 1.28 (s, 1H), 1.09 (s, 4H), 0.85
(d, J = 6.8 Hz, 3H), 0.65 (d, J = 6.9 Hz, 3H). 13C NMR (101 MHz,
d-DMSO) δ 217.44, 164.66, 141.43, 115.87, 72.88, 72.58, 71.77,
68.74, 65.65, 63.78, 57.51, 52.36, 45.39, 44.91, 43.53, 42.00, 37.15,
36.61, 34.44, 32.83, 30.53, 29.45, 27.02, 24.93, 16.58, 14.85, 12.08.
HRMS (ESI) calcd. [M]+ for C27H44NO5 462.3214. Found 462.3217.
Compound 5g
Compound 5g was prepared according to the general procedure from
compound 4g and iodomethane. The crude product was purified over
silica gel column chromatography to give white solid (0.412 g, 70%). IR
(KBr): 3537, 2983, 2960, 2949, 2876, 1742, 1717, 1458, 1406, 1231,
1209, 1153, 1126, 1012, 998 cm−1 1H NMR (400 MHz, d-DMSO) δ
.
6.13 (dd, J = 17.8, 11.2 Hz, 1H), 5.63 (d, J = 8.1 Hz, 1H), 5.22–4.98 (m,
2H), 4.59 (dd, J = 46.0, 17.2 Hz, 3H), 3.82–3.61 (m, 3H), 3.48 (dd,
J = 19.8, 8.2 Hz, 3H), 3.17 (d, J = 1.4 Hz, 3H), 2.48 (s, 1H), 2.31–2.05 (m,
7H), 2.04 (s, 1H), 1.66 (s, 2H), 1.50 (d, J = 15.9 Hz, 2H), 1.37 (s, 3H), 1.30
(s, 2H), 1.09 (s, 4H), 0.85 (d, J = 6.8 Hz, 3H), 0.66 (d, J = 6.9 Hz, 3H).
13C NMR (101 MHz, d-DMSO) δ 217.41, 164.68, 141.45, 115.87,
72.89, 71.74, 65.62, 65.12, 62.40, 57.55, 49.43, 45.39, 44.92, 42.00,
37.18, 36.62, 34.45, 30.57, 29.48, 27.02, 24.93, 21.70, 16.58, 14.89,
12.10. HRMS (ESI) calcd. [M]+ for C27H44NO5 434.3265. Found
434.3274.