Table 3.
1H NMR data for compounds 5 and 6 (600 MHz, CDCl3).
| Position | (9R,10S)-Epoxy-Z-Pinnatifidenyne (5) | Pinnatifidehyde (6) |
|---|---|---|
| δH (J in Hz) | δH (J in Hz) | |
| 1 | 3.17, br.s | |
| 3 | 5.63, br.d (10.8) | |
| 4 | 6.05, ddd (7.6, 7.7, 10.8) | 9.80, br.s |
| 5 | 2.58, dd (5.5, 7.7, 14.2) 2.87, ddd (7.6, 7.6, 14.2) |
2.71, dd (4.0, 18.7) 3.10, br.dd (8.0, 18.7) |
| 6 | 3.79, ddd (2.3, 5.5, 7.6) | 4.46, ddd (2.9, 4.0, 8.0) |
| 7 | 4.11, ddd (2.3, 4.8, 11.7) | 4.00, ddd (2.9, 5.1, 11.8) |
| 8 | 1.94, ddd (11.6, 11.7, 13.2) 2.67, ddd (3.5, 4.8, 13.2) |
2.53, ddd (2.2, 5.1, 12.0) 2.96, ddd (5.1, 6.6, 12.0) |
| 9 | 2.88, ddd (3.5, 4.0, 11.6) | 5.72, ddd (2.2, 6.6, 10.3) |
| 10 | 3.05, ddd (4.0, 4.6, 9.4) | 5.96, br.dd, (8.3, 10.3) |
| 11 | 1.65, ddd (9.4, 10.9, 14.0) 2.58, ddd (3.3, 4.6, 14.0) |
2.31, ddd, (1.4, 8.3, 14.0) 2.64, br.dd, (3.9, 14.0) |
| 12 | 3.66, dd (3.3; 10.9) | 3.67, ddd (1.4, 3.9, 10.3) |
| 13 | 4.00, ddd (3.1, 3.1, 10.9) | 3.84, ddd (2.8, 2.9, 10.3) |
| 14 | 1.73, ddq (3.1, 7.3, 14.5) 2.02, ddq (3.1, 7.3, 14.5) |
1.74, ddq (2.9, 7.3, 14.6) 1.90, ddq (2.8, 7.3, 14.6) |
| 15 | 1.08, t (7.3) | 1.04, t (7.3) |