Table 1.
13C and 1H NMR data for eucalyprobusals A–E (1–5) in CDCl3
| Eucalyprobusal A (1)a | Eucalyprobusal B (2)a | Eucalyprobusal C (3)b | Eucalyprobusal D (4)a | Eucalyprobusal E (5)a | ||||||
|---|---|---|---|---|---|---|---|---|---|---|
| No. | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) |
| 1 | 76.5 | 75.9 | 72.7 | 82.4 | 76.3 | |||||
| 2 | 132.6 | 5.88 d (9.8) | 133.4 | 5.79 d (10.0) | 80.2 | 4.49 d (5.3) | 195.5 | 150.0 | 6.81 d (10.1) | |
| 3 | 135.9 | 5.83 dd (9.8, 1.0) | 135.3 | 5.83 d (10.0) | 111.6 | 5.10 d (5.3) | 121.9 | 5.85 s | 130.6 | 6.05 d (10.1) |
| 4 | 72.8 | 72.6 | 155.2 | 168.7 | 196.9 | |||||
| 5α | 27.0 | 1.54 dd (13.4, 2.4) | 35.4 | 1.51 brd (13.2) | 32.4 | 2.62 dd (18.8, 6.3) | 32.9 | 2.73 ddd (19.4, 5.6) | 40.4 | 2.64 dd (20.1, 7.5) |
| 5β | 1.38t (13.4) | 1.41 dd (13.2, 2.5) | 1.86 brd (18.8) | 2.46 brd (3.7) | 2.52t (7.5) | |||||
| 6 | 33.1 | 2.26 ddd (13.4, 6.2, 3.0) | 33.5 | 2.36 brdd (13.2, 3.2) | 40.2 | 2.23 brt (4.8) | 44.0 | 2.49 m | 35.0 | 2.54 m |
| 7 | 23.7 | 1.39 s | 27.2 | 1.55 s | 26.4 | 1.65 s | 22.5 | 1.63 s | 25.4 | 1.67 s |
| 8 | 37.8 | 1.76 sept (6.8) | 37.6 | 1.71 sept (6.8) | 34.5 | 2.06 sept. (6.8) | 35.6 | 2.43 sept. (6.8) | ||
| 9 | 16.2 | 0.93 d (6.8) | 16.2 | 0.92 d (6.8) | 21.1 | 0.74 d (6.8) | 20.5 | 1.13 d (6.8) | ||
| 10 | 17.3 | 0.87 d (6.8) | 17.3 | 0.83 d (6.8) | 20.9 | 0.72 d (6.8) | 20.7 | 1.12 d (6.8) | ||
| 1′ | 163.5 | 161.6 | 165.0 | 163.9 | 171.7 | |||||
| 2′ | 104.2 | 104.0 | 109.1 | 104.6 | 99.3 | |||||
| 3′ | 168.0 | 168.1 | 167.3 | 167.6 | 160.3 | |||||
| 4′ | 104.2 | 104.1 | 105.6 | 104.8 | 103.7 | |||||
| 5′ | 171.2 | 170.1 | 169.1 | 169.1 | 168.1 | |||||
| 6′ | 103.1 | 103.8 | 117.4 | 106.2 | 103.6 | |||||
| 7′a | 192.3 | 9.96 s | 192.3 | 9.99 s | 193.7 | 10.10 s | 192.6 | 10.14 s | 21.5 | 2.41 dd (16.9, 6.0) |
| 7′b | 2.81 dd (16.9, 6.0) | |||||||||
| 8′ | 191.8 | 10.14 s | 191.7 | 10.16 s | 192.3 | 10.21 s | 192.2 | 10.15 s | 191.4 | 10.04 s |
| 9′ | 28.4 | 3.21 ddd (10.9, 6.2, 3.9) | 34.0 | 2.64 brdd (10.2, 3.2) | 35.9 | 3.52 dt (8.2, 4.9) | 31.2 | 2.66 ddd (9.8, 6.3, 3.5) | 206.6 | |
| 10′a | 35.7 | 2.52 ddd (14.5, 10.9, 3.9) | 43.3 | 1.80 ddd (13.1, 10.2, 3.2) | 46.7 | 1.42 brdd (13.5, 6.8) | 43.6 | 1.61 2H m | 52.7 | 2.98 2H d (6.7) |
| 10′b | 1.26 ddd (14.2, 10.9, 3.9) | 1.58 ddd (14.2, 10.2, 3.2) | 1.27 brdd (13.5, 7.7) | |||||||
| 11′ | 24.5 | 1.75 m | 26.6 | 1.87 m | 25.6 | 1.47 m | 25.6 | 1.67 m | 27.5 | 1.92 m |
| 12′ | 20.9 | 1.00 d (6.5) | 21.6 | 1.01 d (6.5) | 22.3 | 0.93 d (6.3) | 22.2 | 0.97 d (6.4) | 22.7 | 0.98 d (6.7) |
| 13′ | 24.3 | 0.96 d (6.5) | 23.6 | 0.96 d (6.5) | 22.8 | 0.85 d (6.3) | 24.0 | 0.85 d (6.4) | 22.7 | 0.98 d (6.7) |
| OH-3′ | 13.43 s | 13.44 s | 13.29 s | 13.35 s | OH-1′ | 15.48 s | ||||
| OH-5′ | 13.82 s | 13.48 s | 13.31 s | 13.38 s | OH-5′ | 14.45 s | ||||
a
Data were recorded at 500 MHz.
b
Data were recorded at 800 MHz.