Table 1 1H NMR (400 MHz, CDCl3; δH, J in Hz) data for compounds 1–9
Position | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
|---|---|---|---|---|---|---|---|---|---|
1 | |||||||||
2 | 7.42 (d, 8.6) | 7.26 (d, 2.4) | 7.00 (d, 8.6) | 6.96 (d, 8.7) | 7.17 (d, 8.4) | 7.19 (d, 8.6) | 7.21 (d, 8.5) | 6.93 (br s) | 6.92 (br s) |
3 | 7.04 (d, 8.6) | 6.43 (d, 8.6) | 6.36 (d, 8.7) | 6.72 (d, 8.4) | 6.72 (d, 8.6) | 6.79 (d, 8.5) | |||
4 | |||||||||
5 | 7.04 (d, 8.6) | 6.97 (d, 8.5) | 6.43 (d, 8.6) | 6.36 (d, 8.7) | 6.72 (d, 8.4) | 6.72 (d, 8.6) | 6.79 (d, 8.5) | 6.86, overlapped | 6.85, overlapped |
6 | 7.42 (d, 8.6) | 7.34 (dd, 8.5, 2.4) | 7.00 (d, 8.6) | 6.96 (d, 8.7) | 7.17 (d, 8.4) | 7.19 (d, 8.6) | 7.21 (d, 8.5) | 6.85, overlapped | 6.85, overlapped |
7 | 6.33 (d, 16.2) | 6.29 (d, 16.3) | 6.13 (d,16.3) | 6.11 (d, 16.2) | 6.18 (d, 16.2) | 6.25 (d, 16.2) | 6.26 (d, 16.2) | 6.19 (d, 16.2) | 6.19 (d, 16.2) |
8 | 6.20 (d, 16.2) | 6.11 (d, 16.3) | 5.95 (d, 16.3) | 5.93 (d, 16.2) | 5.99 (d, 16.2) | 6.08 (d, 16.2) | 6.09 (d, 16.2) | 6.03 (d, 16.2) | 6.03 (d, 16.2) |
9 | |||||||||
10 | 1.53 (m) | 1.50 (m) | 1.45 (m) | 1.45 (m) | 1.46 (m) | 1.49 (m) | 1.50 (m) | 1.46 (m) | 1.46 (m) |
11 | 1.98 (m) | 1.96 (m) | 1.92 (m) | 1.91 (m) | 1.93 (m) | 1.94 (m) | 1.95 (m) | 1.93 (m) | 1.93 (m) |
12 | 5.12 (m) | 5.10 (m) | 5.09 (br t, 7.1) | 5.08 (br t, 6.9) | 5.08 (br t, 7.3) | 5.10 (br t, 7.3) | 5.10 (br t, 7.3) | 5.09 (br t) | 5.09 (br t) |
13 | |||||||||
14 | 1.60 (s) | 1.58 (s) | 1.57 (s) | 1.66 (s) | 1.56 (s) | 1.58 (s) | 1.58 (s) | 1.57 (s) | 1.57 (s) |
15 | 1.68 (s) | 1.67 (s) | 1.66 (s) | 1.56 (s) | 1.66 (s) | 1.67 (s) | 1.67 (s) | 1.67 (s) | 1.67 (s) |
16 | 1.23 (s) | 1.20 (s) | 1.15 (s) | 1.14 (s) | 1.15 (s) | 1.19 (s) | 1.19 (s) | 1.17 (s) | 1.17 (s) |
17 | 5.87 (dd, 17.6, 11.0) | 5.88 (dd, 17.4, 10.7) | 5.84 (dd, 17.2, 10.8) | 5.83 (dd, 17.2, 10.8) | 5.84 (dd, 17.7, 10.7) | 5.87 (dd, 17.5, 10.9) | 5.87 (dd, 17.5, 10.8) | 5.85 (dd, 17.6, 10.7) | 5.85 (dd, 17.6, 10.7) |
18a | 5.04 (dd, 17.6, 1.3) | 5.02 (dd, 17.4, 1.4) | 4.97 (dd, 17.2, 1.4) | 4.97 (dd, 17.2, 1.4) | 4.96 (dd, 17.7, 1.3) | 5.01 (dd, 17.5, 1.3) | 5.01 (dd, 17.5, 1.3) | 5.01 (dd, 10.7, 1.3) | 5.01 (dd, 10.7, 1.3) |
18b | 5.08 (dd, 11.0, 1.3) | 5.04 (dd, 10.7, 1.4) | 5.00 (dd, 10.8, 1.4) | 5.00 (dd, 10.8, 1.4) | 5.00 (dd, 10.7, 1.3) | 5.03 (dd, 10.9, 1.3) | 5.02 (dd, 10.8, 1.3) | 4.99 (dd, 17.6, 1.3) | 4.99 (dd, 17.6, 1.3) |
1′ | |||||||||
2′ | 7.26 (d, 2.4) | 7.00 (d, 8.6) | 7.01 (d, 8.7) | 7.16 (d, 8.7) | 7.24 (d, 8.5) | 7.18 (d, 8.4) | 7.19 (br d, 8.6) | 7.16 (br d, 8.6) | |
3′ | 5.68 (s) | 6.56 (d, 8.6) | 6.56 (d, 8.7) | 6.71 (d, 8.7) | 6.77 (d, 8.5) | 6.74 (d, 8.4) | 6.73 (br d, 8.6) | 6.77 (br d, 8.6) | |
4′ | |||||||||
5′ | 6.97 (d, 8.5) | 6.56 (d, 8.6) | 6.56 (d, 8.7) | 6.71 (d, 8.7) | 6.77 (d, 8.5) | 6.74 (d, 8.4) | 6.73 (br d, 8.6) | 6.77 (br d, 8.6) | |
6′ | 7.34 (dd, 8.5, 2.4) | 7.00 (d, 8.6) | 7.01 (d, 8.7) | 7.16 (d, 8.7) | 7.24 (d, 8.5) | 7.18 (d, 8.4) | 7.19 (br d, 8.6) | 7.16 (br d, 8.6) | |
7′ | 7.43 (s) | 6.29 (d, 16.3) | 2.89 (br dd, 11.7, 10.6) | 2.96 (br dd, 11.7, 10.5) | 5.17 (d, 2.2) | 4.18 (d, 8.7) | 4.30 (d, 3.0) | 4.80 (d, 7.3) | 4.91 (d, 6.1) |
8′ | 6.11 (d, 16.3) | 4.06 (d, 10.6) | 4.05 (d, 10.5) | 3.46 (d, 2.2) | 3.96 (d, 8.7) | 3.54 (d, 3.0) | 3.97 (d, 7.3) | 4.04 (d, 6.1) | |
9′ | |||||||||
10′a | 2.60 (d, 18.7) | 1.50 (m) | 1.98 (m) | 1.72 (m) | 1.86 (m) | 1.76 (m) | 2.32 (m) | 1.76 (m) | 1.55 (m) |
10′b | 2.46(d, 18.7) | 1.56 (m) | 1.64 (m) | 1.62 (m) | 1.76 (m) | 1.49 (m) | 1.30 (m) | 1.44 (m) | |
11′a | 1.96 (m) | 1.79 (dd, 12.3, 3.3), | 1.70 (dd, 11.8, 3.5) | 1.93 (m) | 1.74 (m) | 1.85 (m) | 1.93(m) | 1.83 (m) | |
11′b | 1.96 (m) | 1.55 (dd, 12.3, 3.3) | 1.60 (dd, 11.8, 3.5) | 1.88 (m) | 1.74 (m) | 1.85 (m) | 1.82 (m) | 1.83 (m) | |
12′ | 5.10 (m) | 2.53 (dt, 12.3, 3.3) | 2.47 (dt, 11.8, 3.5) | 4.58 (m) | 3.14 (m) | 4.08 (dd, 3.0) | 5.06 (m) | 5.03 (m) | |
13′ | |||||||||
14′ | 1.78 (s) | 1.58 (s) | 4.57 (br s), 4.54 (br s) | 4.58 (br s) 4.56 (br s) | 4.95 (d, 1.3) 4.91 (d, 1.3) | 0.82 (s) | 1.11 (s) | 1.58 (s) | 1.57 (s) |
15′ | 1.78 (s) | 1.67 (s) | 1.51 (s) | 1.56 (s) | 1.35 (s) | 0.49 (s) | 1.09 (s) | 1.66 (s) | 1.67 (s) |
16′ | 1.44 (s) | 1.20 (s) | 1.04 (s) | 1.30 (s) | 1.10 (s) | 1.10 (s) | 1.17 (s) | 0.62 (s) | 1.07 (s) |
17′ | 5.87 (dd, 10.6, 7.5) | 5.88 (dd, 17.4, 10.7) | 6.43 (dd, 17.2, 10.8) | 5.83 (dd, 17.2, 10.8) | 6.46 (dd, 17.7, 10.9) | 6.15 (dd, 17.5, 10.9) | 6.02 (dd, 17.5, 10.8) | 5.84 (dd, 17.4, 10.8) | 5.48 (dd, 17.7, 11.0) |
18′a | 5.19 (br d, 3.9) | 5.02 (dd, 17.4, 1.4) | 5.20 (dd, 17.2, 1.4) | 5.20 (dd, 17.2, 1.4) | 4.81 (d, 1.6) | 5.14 (dd, 17.5, 1.3) | 5.05 (dd, 17.5, 1.3) | ||
18′b | 5.16 (br d, 10.6) | 5.04 (dd, 10.7, 1.4) | 5.29 (dd, 10.8, 1.4) | 5.29 (dd, 10.8, 1.4) | 4.85 (d, 1.6) | 4.99 (dd, 10.9, 1.3) | 5.02 (dd, 10.8, 1.3) | ||
OCH3 | 3.04 (s) | 3.16 (s) |