Table 1.
1H and 13C NMR (500 and 125 MHz, methanol-d) data for vernodalinol.
| Position | δH (mult., J, Hz) | δ C | gHMBC |
|---|---|---|---|
| 1 | 5.76 (dd, 11.0, 17.5) | 139.7 | 5, 9, 10, 14 |
| 2 | a: 5.21 (d, 11.0)a | 112.9 | 1, 5, 10 |
| b: 5.25 (d, 17.5)a | 1, 5, 10 | ||
| 3 | — | 163.7 | — |
| 4 | — | 131.4 | — |
| 5 | 2.55 (dd, 10.5, 2.0) | 49.2 | 1, 3, 4, 6, 7, 9, 10, 14, 15 |
| 6 | 4.08 (dd, 11.0, 10.5)b | 67.0 | 4, 5, 7, 11, 15 |
| 7 | 2.74 (dd, 11.5, 11.0)b | 52.7 | 5, 6, 8, 9, 11, 12, 13 |
| 8 | 5.38 (dt, 11.5, 11.5, 4.5) | 68.0 | 7, 9, 11, 16 |
| 9 | a: 1.64 (dd, 13.5, 11.5) | 35.9 | 1, 5, 7, 8, 10 |
| b: 2.01 (dd, 13.5, 4.5) | 1, 5, 7, 8, 10 | ||
| 10 | — | 38.1 | — |
| 11 | — | 136.2 | — |
| 12 | — | 166.5 | — |
| 13 | a: 5.79 (d, 1.0) | 127.0 | 7, 8, 11, 12 |
| b: 6.34 (d, 1.0) | 7, 8, 11, 12 | ||
| 14 | a: 4.42 (dd, 12.0, 2.0) | 69.0 | 1, 3, 5, 9, 10 |
| b: 4.76 (d, 12.0) | 1, 3, 5, 9, 10 | ||
| 15 | a: 5.77 (d, 1.0) | 131.2 | 3, 4, 5, 6, 10 |
| b: 6.54 (d, 1.0) | 3, 4, 5, 6, 10 | ||
| 16 | — | 163.3 | — |
| 17 | — | 138.6 | — |
| 18 | 4.19 (dd, 4.0, 2.0) | 58.5 | 16, 17, 19 |
| 19 | a: 5.85 (dd, 4.0, 3.0) | 122.3 | 16, 17, 18 |
| b: 6.19 (dd, 2.0, 3.0) | 16, 17, 18 |
a
The gem-coupled resonance between these two hydrogens is invisible in the spectrum.
b
The coupling constants of H-6 and H-7 are very close and their multiplicities in the spectrum look like triplet, not doublet–doublet.