Table 4. Spectral data of compounds 3a–3i and 4a–4fa
Compound
IR (cmK1
)
GC–MS m/z
1H NMR (CDCl3) d, J (Hz)
13C NMR (CDCl3) d
42.0 (NMe), 51.0 (CO2CH3), 55.1 (MeO), 101.1 (C-20), 106.7
(C-60), 107.0 (C-40), 114.6 (C-2), 129.8 (C-50), 139.6 (C-3), 160.5
(C-10 or C-30), 160.7 (C-30 or C-10), 166.2 (CO2CH3)
42.0 (NMe), 51.0 (CO2CH3), 97.5 (C-40), 101.1 (OCH2O), 106.1
(C-60), 107.9 (C-70), 115.2 (C-2), 139.6 (C-3), 141.9 (C-7a0), 148.
1 (C-3a0), 154.6 (C-50), 166.3 (CO2CH3)
14.7 (OCH2CH3), 42.0 (NMe), 50.9 (CO2CH3), 55.6 (OMe), 64.7
(OCH2CH3), 100.1 (C-20), 104.4 (C-60), 113.6 (C-50), 114.9
(C-2), 139.5 (C-3), 142.7 (C-40), 150.1 (C-30), 153.6 (C-10), 166.3
3a
1759, 1598, 1491, 1439,
1294, 1197, 1153, 1087,
917, 839, 764
2.91 (s, 6H, NMe), 3.60 (s, 3H, CO2Me), 3.74 (s, 3H, OMe),
6.46–6.54 (m, 3H, ArH), 7.10–7.16 (m, 1H, ArH), 7.11 (s, 1H,
H-3)
3c
1695, 1634, 1482, 1436,
1300, 1219, 1173, 1125,
1086, 1036
265 (MC), 234, 206 (100),
188, 178, 149, 116, 107, 84,
65
2.93 (s, 6H, NMe), 3.60 (s, 3H, CO2Me), 5.86 (s, 2H, OCH2O),
6.34 (dd, JZ8.7, 2.4 Hz, 1H, H-60), 6.50 (d, JZ2.4 Hz, 1H, H-40),
6.64 (d, JZ8.7 Hz, 1H, H-70), 7.08 (s, 1H, H-3)
3d
1695, 1633, 1506, 1440,
1358, 1299, 1220, 1190,
1154, 1120, 1087, 1034
295 (MC), 236 (100), 208,
1.34 (t, JZ7.0 Hz, 3H, OCH2CH3), 2.90 (s, 6H, NMe), 3.57 (s,
190, 179, 153, 139, 116, 88, 3H, CO2Me), 3.77 (s, 3H, OMe), 3.95 (q, JZ7.0 Hz, 2H,
OCH2CH3), 6.33 (dd, JZ8.9, 2.9 Hz, 1H, H-60), 6.53 (d,
84, 57, 42
JZ2.9 Hz, 1H, H-20), 6.70 (d, JZ8.9 Hz, 1H, H-50), 7.08 (s, 1H, (CO2Me)
H-3)
3e
3f
1695, 1634, 1505, 1445,
1358, 1299, 1218, 1189,
1119, 1086, 1025
357 (MC), 298, 266, 238,
210, 153, 116, 91 (100), 65
2.93 (s, 6H, NMe), 3.61 (s, 3H, CO2Me), 3.83 (s, 3H, OMe), 5.04 42.0 (NMe), 51.0 (CO2CH3), 55.7 (OMe), 71.7 (OCH2Ph), 100.3
(s, 2H, OCH2Ph), 6.35 (dd, JZ8.8, 2.7 Hz, 1H, H-60), 6.59 (d,
JZ2.7 Hz, 1H, H-20), 6.76 (d, JZ8.8 Hz, 1H, H-50), 7.11 (s, 1H,
H-3), 7.23–7.44 (m, 5H, PhH)
(C-20), 104.5 (C-60), 114.9 (C-2), 115.1 (C-50), 127.2 (PhCH),
127.6 (PhCH), 128.3 (PhCH), 137.4 (PhC), 139.6 (C-3), 142.7
(C-40), 150.6 (C-30), 154.2 (C-10), 166.2 (CO2Me)
1696, 1638, 1483, 1432,
1359, 1299, 1245, 1220,
1093, 1054
311 (MC), 252 (100), 224,
195, 166, 137, 116, 84, 56,
42
2.95 (s, 6H, NMe), 3.59 (s, 3H, CO2Me), 3.77 (s, 3H, OMe), 3.90 42.0 (NMe), 51.0 (CO2CH3), 56.1 (OMe), 61.1 (OMe), 61.2
(OMe), 106.2 (ArCH), 107.7 (ArCH), 114.9 (C-2), 139.7 (C-3),
(s, 3H, OMe), 3.95 (OMe), 6.46–6.55 (m, 2H, H-50, H-60), 7.13 (s,
1H, H-3)
142.8 (ArC), 143.2 (ArC), 147.0 (ArC), 147.8 (ArC), 166.2
(CO2Me)
3g
3h
3i
1697, 1634, 1486, 1434,
1358, 1299, 1253, 1218,
1146, 1116, 1087, 775
1698, 1637, 1506, 1434,
1359, 1299, 1253, 1218,
1123, 1085
235 (MC), 204, 176 (100),
158, 148, 119, 116, 84, 77,
65
249 (MC, 100), 218, 190,
174, 162, 144, 129, 114, 98,
84, 70
271 (MC), 240, 212 (100),
194, 184, 155, 141, 127,
115, 84, 56, 42
2.30 (s, 3H, Me), 2.95 (s, 6H, NMe), 3.62 (s, 3H, CO2Me),
6.70–6.80 (m, 3H, ArH), 7.10–7.18 (m, 1H, H-50), 7.14 (s, 1H,
H-3)
21.5 (Me), 42.0 (NMe), 51.2 (CO2CH3), 111.7 (C-60), 114.9
(C-2), 115.5 (C-20), 122.3 (C-40), 129.2 (C-50), 139.5 (C-30), 139.
6 (C-3), 159.2 (C-10), 166.1 (CO2Me)
2.26 (br s, 6H, Me), 2.95 (s, 6H, NMe), 3.61 (s, 3H, CO2Me), 6.59 15.8 (Me-2), 21.3 (Me-5), 42.0 (NMe), 51.1 (CO2CH3), 113.1
(d, JZ1.5 Hz, 1H, H-60), 6.67 (dd, JZ7.8, 1.5 Hz, 1H, H-40), 7.01 (C-60), 115.1 (C-2), 121.7 (C-40), 122.8 (C-20), 130.5 (C-30), 136.
(d, JZ7.8 Hz, 1H, H-30), 7.16 (s, 1H, H-3)
5 (C-50), 139.5 (C-3), 157.2 (C-10), 166.7 (CO2Me)
42.1 (NMe), 51.2 (CO2CH3), 108.8 (C-10), 114.8 (C-2), 117.7
(C-30), 123.7 (C-60), 126.3 (C-80), 126.8 (C-50), 127.6 (C-70), 129.
4 (C-4a0), 129.6 (C-40), 134.4 (C-8a0), 139.8 (C-3), 157.2 (C-20),
166.6 (CO2Me)
24.6 (COCH3), 42.7 (NMe), 55.1 (2MeO), 93.5 (C-20, C-40, C-60),
125.5 (C-3), 138.5 (C-4), 161.0 (C-10), 161.5 (C-30, C-50), 194.1
(COCH3)
1696, 1631, 1511, 1435,
1356, 1299, 1215, 1118,
1085, 848, 746
2.96 (s, 6H, NMe), 3.63 (s, 3H, CO2Me), 7.22 (d, JZ2.4 Hz, 1H,
H-10), 7.24 (s, 1H, H-3), 7.26 (dd, JZ8.7, 2.4 Hz, 1H, H-30),
7.29–7.36 (m, 1H, H-60), 7.38–7.45 (m, 1H, H-70), 7.70 (d,
JZ8.1 Hz, 1H, H-80), 7.74–7.80 (m, 2H, H-40, H-50)
1.92 (br s, 3H, COMe), 2.91 (br s, 6H, NMe2), 3.67 (br s, 6H,
2OMe), 6.05 (br s, 3H, H-20, H-40, H-60), 7.20 (br s, 1H, H-4)
4a
4b
4c
4d
4e
1667, 1595, 1470, 1350,
1309, 1203, 1138, 1062,
951
1666, 1592, 1501, 1463,
1422, 1311, 1222, 1126,
1008, 955
1.95 (br s, 3H, COMe), 2.95 (s, 6H, NMe2), 3.71 (s, 3H, OMe),
24.7 (COCH3), 42.3 (NMe), 55.9 (2MeO), 60.7 (MeO), 91.8
3.75 (s, 6H, 2OMe), 6.11 (s, 2H, H-20, H-60), 7.23 (br s, 1H, H-4) (C-20, C-60), 125.5 (C-3), 132.3 (C-40), 138.7 (C-4), 153.8 (C-30,
C-50), 155.5 (C-10), 194.5 (COCH3)
24.7 (COCH3), 42.0 (NMe), 55.8 (MeO), 56.2 (MeO), 99.8
1666, 1588, 1507, 1436,
1308, 1226, 1191, 1153,
1122, 1025, 949
1.96 (br s, 3H, COMe), 2.95 (s, 6H, NMe2), 3.78 (s, 3H, OMe),
3.81 (s, 3H, OMe), 6.33–6.40 (m, 1H, H-60), 6.52 (d, JZ3.0 Hz, (C-20), 104.5 (C-60), 111.8 (C-50), 125.9 (C-3), 138.6 (C-4), 143.7
1H, H-20), 6.72 (d, JZ8.7 Hz, 1H, H-50), 7.23 (br s, 1H, H-4)
1.96 (br s, 3H, COMe), 2.96 (s, 6H, NMe2), 5.89 (s, 2H, OCH2O),
6.32 (dd, JZ8.1, 2.4 Hz, 1H, H-60), 6.49 (d, JZ2.4 Hz, 1H, H-40),
6.66 (d, JZ8.1 Hz, 1H, H-70), 7.22 (br s, 1H, H-4)
1.84 (br s, 3H, COMe), 2.83 (s, 6H, NMe2), 3.62 (s, 3H, OMe),
6.32–6.47 (m, 3H, H-20, H-40, H-60), 6.97–7.08 (m, 1H, H-50),
7.14 (br s, 1H, H-4)
(C-40), 149.9 (C-30), 153.4 (C-10), 192.6 (COCH3)
24.7 (COCH3), 42.0 (NMe), 97.5 (C-40), 101.2 (OCH2O), 106.0
(C-60), 108.1 (C-70), 126.1 (C-3), 138.5 (C-4), 142.0 (C-7a0), 148.
4 (C-3a0), 153.4 (C-50), 194.2 (COCH3)
24.3 (COCH3), 41.9 (NMe), 54.8 (MeO), 100.7 (C-20), 106.5
(C-40 or C-60), 106.7 (C-60 or C-40), 125.2 (C-3), 129.8 (C-50),
138.1 (C-4), 159.9 (C-10 or C-30), 160.6 (C-30 or C-10), 193.8
(COCH3)
1667, 1588, 1481, 1307,
1173, 1125, 1035
1666, 1603, 1589, 1577,
1488, 1434, 1352, 1310,
1140, 1119, 1042, 963
1.93 (br s, 3H, COMe), 2.24 (s, 3H, Me-50), 2.25 (s, 3H, Me-20), 15.8 (CH3-20), 21.2 (CH3-50), 24.5 (COCH3), 42.0 (NMe), 112.8
2.96 (s, 6H, NMe2), 6.58 (br s, 1H, H-60), 6.67 (br d, JZ7.5 Hz, (C-60), 121.8 (C-20), 122.5 (C-40), 125.5 (C-3), 130.7 (C-30),
4f
1666, 1589, 1505, 1434,
1353, 1313, 1253, 1123,
959
1H, H-40), 7.02 (d, JZ7.5 Hz, 1H, H-30), 7.30 (br s, 1H, H-4)
136.9 (C-50), 138.4 (C-4), 156.7 (C-10), 194.8 (COCH3)
a For spectral data of 3b, see Ref. 10.