Table 1.
1H and 13C NMR data for (±)-1‒3 in MeOH-d4.
| No. | (±)-1 |
(±)-2 |
(±)-3 |
|||
|---|---|---|---|---|---|---|
| δH (J in Hz)a | δCb | δH (J in Hz)a | δCb | δH (J in Hz)a | δCb | |
| 1 | 7.80 s | 109.8 | 8.19 s | 102.8 | 7.81 s | 109.7 |
| 2 | 150.0 | 154.2 | 150.0 | |||
| 3 | 158.0 | 158.4 | 158.1 | |||
| 4 | 7.03 s | 110.5 | 7.57 s | 105.1 | 7.04 s | 110.5 |
| 4a | 138.1 | 140.5 | 138.3 | |||
| 5 | 3.25 ddd (16.8, 8.4, 6.6) | 27.3 | 8.08 d (6.6) | 123.8 | 3.26 ddd (16.8, 8.4, 6.6) | 27.3 |
| 3.13 ddd (16.8, 10.8, 6.6) | 3.15 ddd (16.8, 10.8, 6.6) | |||||
| 6 | 4.33 ddd (15.0, 10.8, 6.6) | 49.2 | 8.66 d (6.6) | 132.7 | 4.34 ddd (15.0, 10.8, 6.6) | 49.6 |
| 4.16 ddd (15.0, 8.4, 6.6) | 4.17 ddd (15.0, 8.4, 6.6) | |||||
| 8 | 5.78 d (3.6) | 64.5 | 6.53 (3.6) | 65.2 | 5.77 d (3.6) | 64.1 |
| 8a | 115.5 | 115.3 | 114.2 | |||
| 9 | 145.0 | 145.3 | 145.6 | |||
| 10 | 150.0 | 149.8 | 149.8 | |||
| 11 | 6.93 d (7.8) | 110.2 | 6.93 d (7.8) | 110.4 | 6.92 d (7.8) | 110.0 |
| 12 | 6.97 d (7.8) | 120.7 | 7.03 d (7.8) | 120.6 | 7.04 d (7.8) | 121.8 |
| 12a | 127.5 | 129.3 | 126.9 | |||
| 13 | 5.80 d (3.6) | 46.0 | 6.17 d (3.6) | 43.5 | 5.40 d (3.6) | 48.1 |
| 13a | 176.2 | 154.6 | 175.9 | |||
| 13b | 118.6 | 124.7 | 118.5 | |||
| 2′ | 4.63 dd (8.4, 3.6) | 60.2 | 4.63 dd (8.4, 3.6) | 60.4 | 4.27 dd (8.4, 3.6) | 55.9 |
| 3′ | 3.38 m | 44.1 | 3.34 m | 44.4 | 3.43 m | 38.3 |
| 4′a | 2.23 ddd (20.4, 13.8, 10.2) | 27.1 | 2.31 ddd (20.4, 13.8, 10.2) | 27.2 | 2.60 dd (18.6, 10.8) | 32.9 |
| 4′b | 1.65 ddt (13.8, 7.8, 1.8) | 1.81 ddt (13.8, 7.8, 1.8) | 1.80 dd (18.6, 3.6) | |||
| 5′a | 3.43 td (10.2, 2.4) | 48.9 | 3.50 td (10.2, 2.4) | 48.9 | 178.0 | |
| 5′b | 1.94 td (10.2, 7.8) | 2.10 td (10.2, 7.8) | ||||
| 6′ | 172.0 | 172.1 | ||||
| 7′ | 1.93 s | 22.5 | 1.98 s | 22.6 | ||
| 2,3-OCH2O- | 6.23 s | 105.0 | 6.41 s | 105.8 | 6.23 d (1.2) | 105.1 |
| 6.21 s | 6.39 s | 6.21 d (1.2) | ||||
| 9,10-OCH2O- | 6.14 s | 104.0 | 6.17 d (1.2) | 104.1 | 6.13 d (1.2) | 104.1 |
| 6.11 s | 6.09 d (1.2) | 6.10 d (1.2) | ||||
1H NMR data (δ) were measured in 600 MHz NMR instrument. Proton coupling constants (J) in Hz are given in parentheses.
Data were recorded at 150 MHz. The assignments were based on 1H‒1H COSY, HSQC, HMBC, and NOESY experiments.