1H NMR data (400 MHz) of compounds 5–9a.
| Position | 5b | 6b | 7b | 8c | 9b |
|---|---|---|---|---|---|
| 3 | 6.50 s | 7.08 s | 7.07 s | 6.91 s | |
| 4 | 2.68d | 2.94 dd (14.9, 2.5) | 7.76 d (5.2) | 7.82 s | 2.73e |
| 3.14d | 3.22e | 2.86e | |||
| 5 | 2.64d | 3.20e | 8.56 d (5.2) | 3.27e | |
| 3.09d | 3.59 brdd (12.6, 5.3) | 4.12 brdd (13.2, 2.0) | |||
| 6a | 3.20 dd (14.1, 4.5) | 4.11 dd (13.9, 4.3) | 4.97 dd (13.8, 3.8) | ||
| 7 | 2.19 dd (14.5, 14.1) | 2.87 dd (13.9, 13.8) | 2.79 t (13.8) | ||
| 3.69 dd (14.5, 4.5) | 3.03 dd (13.8, 4.3) | 2.96 dd (13.8, 3.8) | |||
| 8 | 7.31 dd (7.1, 1.2) | 8.03 s | 7.25–7.32e | ||
| 9 | 7.26 ddd (7.5, 7.1, 1.2) | 7.25–7.32e | |||
| 10 | 6.71 d (8.4) | 7.32 ddd (7.6, 7.5, 1.2) | 7.15 d (8.8) | 7.30 d (9.0) | 7.25–7.32e |
| 11 | 7.46 d (8.4) | 8.33 brd (7.6) | 8.19 d (8.8) | 8.66 d (9.0) | 8.30 brd (7.7) |
| OCH2O | 5.88 d (1.1) | ||||
| 6.02 d (1.1) | 6.28 s | 6.40 s | |||
| 1-OCH3 | 3.72 s | 3.53 s | |||
| 3-OCH3 | 4.03 s | ||||
| 5-OCH3 | 3.82 s | ||||
| 8-OCH3 | 3.92 s | ||||
| 9-OCH3 | 4.03 s | ||||
| 2-OCOCH3 | 2.32 s | ||||
| N–CH3 | 2.64 s | ||||
| N–COCH3 | 2.21 s | ||||
| 1′ | 4.96 d (7.6) | ||||
| 2′ | 3.54 dd (8.9, 7.6) | ||||
| 3′ | 3.48 t (8.9) | ||||
| 4′ | 3.38 dd (8.9, 8.6) | ||||
| 5′ | 3.48 brdd (8.6, 6.0) | ||||
| 6′ | 3.69 dd (12.0, 6.0) | ||||
| 3.92 dd (12.0, 2.1) |
Assignments were based on 1H–1H COSY, HMQC, HMBC, and NOESY experiments; chemical shifts (δ) are given in ppm.
Recorded in CDCl3.
Recorded in CD3OD.
Overlapping signal.
Partially overlapping signal.