Table 2.
1H (600 MHz) and 13C NMR (150 MHz) spectroscopic data for compounds 1–3 in CDCl3.
| Position |
1 |
2 |
3 |
||||||
|---|---|---|---|---|---|---|---|---|---|
| δH (multi, J in Hz) | δC | HMBC | δH (multi, J in Hz) | δC | HMBC | δH (multi, J in Hz) | δC | HMBC | |
| 1 | 183.4 | 192.2 | 196.8 | ||||||
| 2 | 6.90 (s, 1H) | 135.7* | 3, 4, 12a, 12b, 13, 14 | 3.46 (d, 1H, 13.2) | 50.8 | 1, 3, 4, 12b, 13 | 3.05 (d, 1H, 15.1) | 49.9 | 1, 3, 13 |
| 3.34 (d, 1H, 13.2) | 1, 3, 4, 13 | 2.82 (dd, 1H, 15.1, 3.0) | 1, 3, 4, 12b | ||||||
| 3 | 155.6 | 81.2 | 76.6 | ||||||
| 4 | 182.7 | 199.9 | 3.08 (d, 1H, 16.5) | 39.8 | 2, 3, 4a, 5, 12b, 13 | ||||
| 2.97 (dd, 1H, 16.5, 3.0) | 2, 3 | ||||||||
| 4a | 140.0 | 140.4 | 151.0 | ||||||
| 5 | 7.87 (s, 1H) | 120.4** | 4, 6, 6a, 7, 12b | 7.78 (s, 1H) | 120.6 | 4, 6a, 12b | 7.01 (s, 1H) | 122.3 | 4, 6, 6a, 12b |
| 6 | 164.7 | 164.4 | 163.7 | ||||||
| 6-OH | 12.5 s | 4a, 6, 6a, 7 | 12.42 s | 4a, 6, 6a | 12.3 s | 5, 6, 6a | |||
| 6a | 120.4** | 121.2 | 116.6 | ||||||
| 7 | 192.6 | 192.5* | 192.6 | ||||||
| 7a | 115.2 | 115.1 | 115.0 | ||||||
| 8 | 162.5 | 162.7 | 162.0 | ||||||
| 8-OH | 11.55 s | 7, 7a, 8, 9, 10 | 11.54 s | 7a, 8, 9 | 11.86 s | 7a, 8, 9 | |||
| 9 | 7.31 (dd, 1H, 7.2, 3) | 124.3 | 7a, 8, 11 | 7.33 (dd, 1H, 8.4, 1.2) | 124.7 | 7a, 8, 11 | 7.25 (m, 1H) | 124.0 | 7a, 8, 11, 11a |
| 10 | 7.75 (overlapped, 1H) | 138.6 | 8, 11a, 12 | 7.75 (t, 1H, 7.8) | 138.8 | 8, 11a | 7.67 (m, 1H) | 137.7 | 8 |
| 11 | 7.74 (overlapped, 1H) | 120.3** | 7a, 9, 11a | 7.72 (dd, 1H, 7.8, 1.8) | 120.7 | 7a, 9, 12 | 7.67 (m, 1H) | 120.1 | 7a, 9, 10, 12 |
| 11a | 135.8* | 135.4 | 135.4 | ||||||
| 12 | 182.7 | 182.1 | 183.0 | ||||||
| 12a | 138.9 | 138.4* | 137.6 | ||||||
| 12b | 127.2 | 131.7 | 129.4 | ||||||
| 13 | 3.20 (m, 1H) | 27.3 | 2, 3, 4, 14 | 1.82 (m, 1H) | 33.6 | 15 | 1.87 (pentet, 1H, 6.9) | 38.2 | 2, 3, 4, 14, 15 |
| 14-CH3 | 1.23 (s, 3H) | 21.4 | 3, 13, 15 | 1.08 (d, 3H, 6.0) | 15.5 | 3, 13, 15 | 1.04 (d, 3H, 6.9) | 16.8 | 3, 13, 15 |
| 15-CH3 | 1.21 (s, 3H) | 21.4 | 3, 13, 14 | 0.77 (d, 3H, 6.0) | 16.5 | 3, 13, 14 | 1.04 (d, 3H, 6.9) | 16.8 | 3, 13, 14 |
*, ** chemical shifts can't be assigned.