Table 2.
NMR spectroscopic data of 16-desmethylgymnodimine D (1). * Position numbering is analog to gymnodimine D.
| Position * | δ (13C)/ppm | δ (1H)/ppm | COSY | HSQC-TOCSY H -> C |
HMBC H -> C |
|
|---|---|---|---|---|---|---|
| 1 | 175.5 | |||||
| 2 | 130.2 | |||||
| 3 | 148.6 | 7.05 | 4, 26 | 4, 26 | 1, 2, 4, 26 | |
| 4 | 81.6 | 5.93 | 3, 26 | 3, 26 | 2, 3, 5, 6, 25 | |
| 5 | 125.9 | |||||
| 6 | 136 | (by HMBC) | ||||
| 7 | 43.6 | 3.16 | 8, 24 | 8, 25, 27 | 5, 6, 8, 9, 22, 23 | |
| 8 | 31.8 | 1.9 | 1.43 | 8 | 7, 11 | 11, 13 |
| 9 | 71.6 | 3.66 | 10, 11 | 10, 8 | 7, 8, 10 | |
| 10 | 83.4 | 3.94 | 9, 15 | 9, 15, 8 | 8, 9, 12, 14 | |
| 11 | 27 | 1.79 | 1.56 | 10 | 8, 9, 12 | 9 |
| 12 | 24.9 | 1.77 | 13 | 13,14,15 | ||
| 13 | 78.6 | 4.36 | 11, 14 | 11, 14, 16 | 14, 12 | |
| 14 | 82.5 | 4.13 | 16 | 11, 13, 16 | 12, 13 | |
| 15 | 29.4 | 1.99 | 1.76 | 12 | 9, 14 | |
| 16 | 32.1 | 1.79 | 15 | 14, 15 | ||
| 17 | 82.9 | 4.15 | 15 | 12, 15, 16 | 18, 19, 28 | |
| 18 | 133.1 | |||||
| 19 | 124.9 | 5.99 | 17, 20, 21, 28 | 20, 21 | 18, 28, 17, 20, 21 | |
| 20 | 21.9 | 3 | 2.1 | 21, 20, 19 | 19, 21, 29 | 18, 19, 21, 22 |
| 21 | 31.8 | 2.76 | 20 | 20 | 19, 20, 22 | |
| 22 | 173.3 | |||||
| 23 | 42.7 | |||||
| 24 | 33.6 | 1.59 | 1.37 | 7, 8/21, 25, 25, 27 | 7, 22, 23, 25, 30 | |
| 25 | 19.7 | 1.49 | 1.94 | 27, 30, 24, 32 | ||
| 26 | 11 | 1.99 | 3, 4 | 3, 4 | 1, 2, 3 | |
| 27 | 18.1 | 1.92 | 25, 8, 24, 7 | 5, 6, 7 | ||
| 29 | 15.3 | 1.61 | 20, 21 | 17, 18, 19 | ||
| 30 | 26 | 1.54 | 1.44 | 32, 31 | 23, 32 | |
| 31 | 20.5 | 1.47 | 32, 30, 24? | 23, 32 | ||
| 32 | 50.3 | 3.71 | 3.48 | 32, 31 | 31, 30 | 22, 30, 31 |