Table 1.
1H and 13C NMR data for 1,8a;8b,3a-didehydro-8b-hydroxyptilocaulin (1) and its 8a-OH isomer (2) in CDCl3
| Position | 1 |
2 |
||
|---|---|---|---|---|
| 1H NMR | 13C NMR | 1H NMR | 13C NMR | |
| 2 | 163.5 s | 163.2 s | ||
| 3a | 176.4 s | 175.7 s | ||
| 4 | 2.98 (1H, m) | 34.1 t | 2.98 (1H, m) | 33.9 t |
| 2.64 (1H, dd, 16.8, 8.2Hz) | 2.60 (1H, dd, 16.8, 8.2Hz) | |||
| 5 | 2.34 (1H, m) | 33.4 t | 2.34 (1H, m) | 33.2 t |
| 1.55 (1H, m) | 1.55 (1H, m) | |||
| 5a | 2.91 (1H, m) | 38.3 d | 2.88 (1H, m) | 38.0 d |
| 6 | 1.91 (1H, m) | 35.2 t | 1.76 (1H, td, 12.4, 4.8Hz) | 37.4 t |
| 1.20 (1H, m) | 1.38 (1H, td, 12.4, 11.2Hz) | |||
| 7 | 2.01 (1H, m) | 36.8 d | 2.19 (1H, m) | 42.0 d |
| 8 | 75.4 s | 74.2 s | ||
| 8a | 164.6 s | 163.7 s | ||
| 8b | 125.4 s | 125.4 s | ||
| 1′ | 2.12 (1H, td, 12.4, 4.4Hz) | 37.0 t | 1.92 (1H, m) | 36.9 t |
| 1.85 (1H, td, 12.4, 3.6Hz) | 1.85 (1H, td, 12.4, 3.6Hz) | |||
| 2′ | 1.20 (1H, m) | 27.1 t | 1.11 (1H, m) | 27.1 t |
| 0.91 (1H, m) | 0.72 (1H, m) | |||
| 3′ | 1.25 (2H, m) | 23.5 t | 1.14 (2H, m) | 23.1 t |
| 4′ | 0.83 (3H, t, 7.2Hz) | 14.0 q | 0.78 (3H, t, 7.2Hz) | 13.8 q |
| 5′ | 1.07 (3H, d, 6.8Hz) | 15.1 q | 1.16 (3H, d, 7.2Hz) | 15.7 |