Table 1.
1H- (400 MHz) and 13C- (100 MHz) NMR spectroscopic data of compounds 1–3 in acetone-d6 (δ (ppm), J (Hz)).
| No. | 1 a | 2 b | 3 | |||
|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | |
| 1 | 2.74 dd (11.6, 5.2) | 50.9 d | 2.77 m | 50.9 d | 3.08 m | 52.6 d |
| 2a 2b |
2.06 m 2.27 m |
35.4 t | 2.05 m 2.22 m |
35.9 t | 2.47 m 2.73 dd (18.9, 11.8) |
32.8 t |
| 3 | 3.60 t (5.0) | 82.5 d | 3.53 dd (1.5, 5.1) | 83.0 d | 174.0 s | |
| 4 | 51.4 s | 52.3 s | 62.5 s | |||
| 5 | 84.1 s | 83.1 s | 87.5 s | |||
| 6 | 2.05 m (2H) | 34.0 t | 3.91 overlap | 78.2 d | 6.04 d (9.6) | 69.8 d |
| 7 | 3.62 t (5.0) | 72.4 d | 3.41 overlap | 78.3 d | 5.23 d (9.7) | 68.7 d |
| 8 | 54.5 s | 53.8 s | 56.1 s | |||
| 9 | 2.08 m | 54.6 d | 2.08 m | 49.9 d | 2.32 m | 47.0 d |
| 10 | 78.4 s | 77.7 s | 77.4 s | |||
| 11a 11b |
1.58 m 1.90 m |
21.8 t | 1.71 m 1.81 m |
21.6 t | 1.98 m 2.03 m |
21.1 t |
| 12a 12b |
1.58 m 2.23 m |
27.0 t | 1.68 m 2.35 m |
28.1 t | 1.74 m 2.08 m |
25.8 t |
| 13 | 2.05 overlap | 52.9 d | 2.24 m | 47.6 d | 3.10 overlap | 46.4 d |
| 14 | 5.59 s | 82.1 d | 5.52 s | 76.4 d | 6.43 s | 79.3 d |
| 15 | 4.93 s | 85.0 d | 3.26 s | 68.6 d | 5.27 s | 86.2 d |
| 16 | 79.6 s | 61.3 s | 88.4 s | |||
| 17 | 1.27 s (3H) | 22.8 q | 1.45 s (3H) | 14.6 q | 1.55 s (3H) | 19.4 q |
| 18 | 1.11 s (3H) | 18.5 q | 1.23 s (3H) | 19.3 q | 2.49 d (5.0) 2.98 d (4.9) |
52.8 t |
| 19 | 0.91 s (3H) | 23.0 q | 0.97 s (3H) | 23.2 q | 1.34 s (3H) | 17.4 q |
| 20 | 1.41 s (3H) | 27.8 q | 1.41 s (3H) | 28.2 q | 1.51 s (3H) | 33.6 q |
| 6-OAc | 2.02 s (3H) | 20.6 q | ||||
| 169.4 s | ||||||
| 7-OAc | 2.10 s (3H) | 21.6 q | ||||
| 169.8 s | ||||||
| 14-OPr | 1.11 t (3H, 7.6) 2.85 m (2H) |
9.6 q | 1.08 t (3H, 7.6) 2.27 m (2H) |
9.5 q | 1.08 t (3H, 7.5) 2.36 m (2H) |
9.1 q |
| 28.4 t | 28.5 t | 28.2 t | ||||
| 173.4 s | 173.8 s | 174.0 s | ||||
| 15-OAc | 2.10 s (3H) | 21.0 q | 1.98 s (3H) | 20.8 q | ||
| 170.3 s | 171.6 s | |||||
| 16-OAc | 1.98 s (3H) | 22.7 q | ||||
| 169.8 s | ||||||
a Hydroxyl groups of 1: δH 4.20 (d, J = 5.4 Hz, 3-OH), 3.39 (s, 10-OH), 3.06 (s, 16-OH); b Hydroxyl groups of 2: δH 3.91 (overlap, 3-OH), 3.64 (s, 5-OH), 3.51 (s, 10-OH), 3.41 (overlap, 6-OH), 3.34 (d, J = 7.8 Hz, 7-OH).