Table 1.
1H NMR spectroscopic data of compounds 1–5.
| No. | 1 a | 2 b | 3 a | 4 a | 5 b |
|---|---|---|---|---|---|
| 2 | - | 5.48 d (9.2) c | 5.43 d (8.4) c | 5.89 d (11.2) c | 6.07 d (10.8) c |
| 3 | 5.33 s | 5.22 d (9.2) | 3.53 d (8.4) | 6.29 d (11.2) | 5.98 d (10.8) |
| 5 | a: 2.03 m | a: 2.54 m | a: 2.02 ddd (14.0, 5.6, 2.8) | a: 2.87 m | a: 2.28 m |
| b: 1.95 m | b: 2.19 m | b: 1.08 m | b: 2.83 m | b: 2.24 m | |
| 6 | a: 2.00 m | a: 2.21 m | a: 1.83 m | 5.19 m | a: 1.85 m |
| b: 1.22 m | b: 1.47 m | b: 1.16 m | - | b: 1.79 m | |
| 7 | 2.74 dd (10.0, 3.6) c | 2.57 m | 2.74 dd (10.8, 3.6) | 6.83 br s | 3.01 dd (6.0, 5.6) |
| 9 | a: 1.85 m | a: 2.19 m | a: 1.91 m | a: 2.52 m | a: 2.18 m |
| b: 0.96 dd (16.4, 9.6) | b: 1.08 m | b: 0.80 t (12.4) | b: 2.04 m | b: 1.61 m | |
| 10 | a: 2.09 m | a: 2.59 m | a: 1.84 m | a: 2.31 m | a: 2.18 m |
| b: 1.79 m | b: 2.17 m | b: 1.65 tt (12.4, 6.0) | b: 2.18 m | b: 2.04 m | |
| 11 | 6.85 dd (10.0, 6.8) | 6.80 dd (8.8, 6.4) | 6.83 dd (10.4, 6.4) | 4.66 br d (10.4) | 5.08 br t (6.4) |
| 13 | a: 2.64 td (13.6, 6.4) | a: 2.55 m | a: 2.56 td (12.8, 4.8) | a: 2.22 m | 2.04 m |
| b: 2.49 td (13.6, 3.6) | b: 2.37 m | b: 2.40 td (12.8, 4.8) | b: 2.07 m | - | |
| 14 | a: 2.25 td (13.6, 6.4) | 2.19 m | a: 2.28 td (12.8, 4.8) | a: 2.68 m | 2.29 m |
| b: 1.96 m | - | b: 2.19 td (12.8, 4.8) | b: 1.98 m | - | |
| 15 | - | - | - | - | 2.35 m |
| 16 | a: 3.68 d (10.0) | - | 1.32 s | 1.05 d (6.8) | 1.06 d (6.4) |
| b: 3.38 d (10.0) | - | - | - | - | |
| 17 | 1.11 s | 1.92 s | 1.39 s | 1.14 d (6.8) | 1.07 d (6.4) |
| 18 | 2.00 s | 1.96 s | 1.12 s | a: 4.09 d (13.6) | 1.76 s |
| - | - | - | b: 4.03 d (13.6) | - | |
| 19 | 1.04 s | 1.31 s | 0.93 s | - | a: 3.77 dd (12.0, 6.4) |
| - | - | - | - | b: 3.56 dd (12.0, 4.8) | |
| 20 | - | - | - | 1.51 s | 1.59 s |
| 2-OMe | 3.18 s | - | - | - | - |
| 15-OMe | - | 2.93 s | - | - | |
| 20-OMe | 3.40 s | 3.77 s | 3.40 s | - | - |
| 19-OH | - | - | - | - | 1.62 m |
a Spectra were measured in C6D6 (400 MHz); b Spectra were measured in CDCl3 (400 MHz); c J values (in Hz) are in parentheses.