Table 1.
1H NMR data for compounds 3 and 4 (600 MHz, CDCl3).
| Position | (3R,4S)-Epoxy-Pinnatifidenyne (3) | (3S,4R)-Epoxy-Pinnatifidenyne (4) |
|---|---|---|
| δH (J in Hz) | δH (J in Hz) | |
| 1 | 2.39, d (1.7) | 2.38, d (1.7) |
| 3 | 3.52, dd (1.7, 4.0) | 3.44, dd (1.7, 4.0) |
| 4 | 3.25, ddd (3.8, 4.0, 8.4) | 3.12, ddd (4.0, 4.7, 7.6) |
| 5 | 1.64, ddd (3.3, 8.4, 14.6) 2.35, ddd (3.8, 9.7, 14.6) |
2.06, ddd (4.7, 7.0, 14.5) 2.14, ddd (7.6, 7.6, 14.5) |
| 6 | 4.12, ddd (2.5, 3.3, 9.7) | 4.03, ddd (2.6, 4.7, 7.6) |
| 7 | 3.95, ddd (2.5, 5.0, 11.6) | 4.08, ddd (2.6, 5.1,11.7) |
| 8 | 2,55, ddd (5.0, 6.6, 11.8) 2.96, ddd (1.7, 11.6, 11.8) |
2.56, ddd (5.8, 6.1, 12.5) 2.99, dddd (1.8, 11.6, 12.5) |
| 9 | 5.72, dddd (1.7, 6.6, 10.1) | 5.72, ddd (1.8, 6.1, 10.3) |
| 10 | 5.93, br.dd (8.4, 10.1) | 5.93, br.dd (8.5, 10.3) |
| 11 | 2.44, ddd (1.3, 8.4, 14.0) 2.61, br.dd (3.7, 14.0) |
2.37, ddd (1.0, 8.5, 13.9) 2.62, br.dd (3.8, 13.9) |
| 12 | 3.65, ddd (1.3, 3.7, 10.0) | 3.53, ddd (1.0, 3.8, 10.1) |
| 13 | 3.97, ddd (3.0, 3.3, 10.0) | 3.97, ddd (2.8, 3.5, 10.1) |
| 14 | 1.79, ddq (3.3, 7.2, 14.5) 2.06, ddq (3.0, 7.2, 14.5) |
1.80, ddq (2.8, 7.2, 14.5) 2.04, ddq (3.5, 7.2, 14.5) |
| 15 | 1.08, t (7.2) | 1.08, t (7.2) |