Table 1.
NMR data (800 MHz, CDCl3) for galangalditerpenes A–C (1–3).
| Position | 1 | 2 | 3 | |||
|---|---|---|---|---|---|---|
| δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | |
| 1 | 1.04 (ddd, 3.2, 12.8, 12.8, Hα), 1.87 (ddd, 2.4, 3.2, 12.8, Hβ) | 39.4 | 1.02 (ddd, 4.0, 12.8, 12.8, Hα), 1.76 (m, Hβ) |
39.0 | 0.96 (ddd, 3.6, 12.8, 12.8, Hα), 1.42 (m, Hβ) | 40.5 |
| 2 | 1.60 (m, Hα), 1.51 (ddddd, 2.4, 3.2, 12.8, 13.6, 14.4, Hβ) | 18.6 | 1.76 (ddddd, 2.4, 3.2, 4.0, 4.0, 14.4, Hα), 1.50 (ddddd, 3.6, 4.0, 12.8, 13.4, 14.4, Hβ) | 18.5 | 1.51 (m, Hα), 1.41 (m, Hβ) | 18.3 |
| 3 | 1.19 (ddd, 4.0, 13.6, 13.6, Hα), 1.41 (ddd, 2.4, 2.4, 13.6, Hβ) | 41.6 | 1.20 (ddd, 4.0, 13.4, 13.4, Hα), 1.76 (ddd, 2.4, 3.6, 13.4, Hβ) |
41.8 | 1.17 (ddd, 3.2, 13.6, 13.6, Hα), 1.43 (m, Hβ) | 41.9 |
| 4 | 33.4 | 33.3 | 33.5 | |||
| 5 | 0.96 (dd, 2.4, 12.8) | 55.5 | 0.96 (dd, 2.4, 12.4) | 54.5 | 1.00 (dd, 2.4, 12.0) | 54.2 |
| 6 | 1.74 (dddd, 2.4, 4.4, 4.4, 13.6, Hα), 1.15 (dddd, 2.4, 3.2, 12.8, 13.6, Hβ) | 20.5 | 1.74 (m, Hα), 1.35 (dddd, 4.0, 12.0, 12.4, 12.4, Hβ) | 20.0 | 1.71 (br ddd, ca. 2, 6, 14, Hα), 1.66 (dddd, 4.0, 12.0, 13.6, 14.4, Hβ) | 19.9 |
| 7 | 1.64 (m, Hα), 1.84 (ddd, 2.4, 3.2, 12.8, Hβ) | 40.1 | 1.40 (dddd, 4.0, 12.0, 12.4, 12.4, Hα), 1.74 (m, Hβ) | 26.8 | 1.97 (ddd, 5.6, 13.6, 14.4, Hα), 1.42 (m, Hβ) | 18.3 |
| 8 | 84.7 | 2.28 (dddd, 3.2, 5.6, 12.0, 14.4) | 53.8 | 58.2 | ||
| 9 | 1.64 (m) | 57.4 | 1.54 (ddd, 3.2, 6.4, 14.4) | 50.3 | 1.42 (br d, ca. 10) | 56.9 |
| 10 | 39.5 | 37.5 | 39.5 | |||
| 11 | 2.40 (br dd, ca. 9, 13, Hα), 2.57 (ddd, 8.8, 10.4, 12.8, Hβ) | 24.7 | 1.81 (ddd, 6.4, 9.6, 12.8), 2.40 (ddd, 3.2, 6.4, 12.8) |
29.9 | 6.49 (dd, 10.4, 16.8) | 144.4 |
| 12 | 6.87 (ddd, 2.4, 8.8, 8.8) | 157.6 | 6.62 (dd, 6.4, 9.6) | 139.6 | 6.01 (d, 16.8) | 135.8 |
| 13 | 140.4 | 126.2 | 198.4 | |||
| 14 | 2.27 (ddd, 2.4, 3.2, 16.0, Hα), 3.13 (dd, 5.6, 16.0, Hβ) | 29.6 | 2.70 (m), 2.74 (m) | 25.3 | ||
| 15 | 5.44 (dd, 3.2, 5.6) | 100.4 | 4.34 (ddd, 6.4, 7.2, 14.4), 4.37 (ddd, 6.4, 7.6, 14.4) |
65.4 | ||
| 16 | 9.35 (s) | 194.1 | 171.1 | 2.23 (3H, s) | 26.4 | |
| 17 | 3.62 (d, 9.6, Hα), 4.35 (d, 9.6, Hβ) | 70.4 | 9.28 (d, 5.6) | 203.8 | 2.31 (d, 4.8, Hα), 2.38 (d, 4.8, Hβ) | 48.8 |
| 18 | 0.80 (3H, s) | 21.5 | 0.84 (3H, s) | 21.7 | 0.90 (3H, s) | 21.9 |
| 19 | 0.89 (3H, s) | 33.5 | 0.89 (3H, s) | 33.4 | 0.91 (3H, s) | 33.5 |
| 20 | 0.81 (3H, s) | 14.9 | 0.87 (3H, s) | 14.2 | 1.09 (3H, s) | 15.6 |