Table 1.
NMR spectral data (δ)a for compounds (−)-/(+)-1, 2 and 3.
| (−)-/(+)-1b |
2c |
3d |
||||
|---|---|---|---|---|---|---|
| No. | δH | δC | δH | δC | δH | δC |
| 1 | 119.1 | 118.6 | 117.2 | |||
| 2 | 8.31 d (2.4) | 132.1 | 133.8 | 135.0 | ||
| 3 | 115.8 | 8.57 d (9.0) | 123.5 | 8.76 d (9.0) | 122.4 | |
| 4 | 165.8 | 7.18 dd (9.0, 3.0) | 122.4 | 7.16 dd (9.0, 2.5) | 122.2 | |
| 5 | 6.60 d (9.0) | 116.9 | 154.0 | 153.0 | ||
| 6 | 7.66 dd (9.0, 2.4) | 133.0 | 7.56 d (3.0) | 117.5 | 7.55 d (2.5) | 117.0 |
| 7 | 169.8e | 169.4 | 169.1 | |||
| 8 | 170.4 | |||||
| 1′ | 134.8 | 116.1 | 135.8 | |||
| 2′ | 7.48 d (1.8) | 113.5 | 162.8 | 8.01 d (7.0) | 127.6 | |
| 3′ | 148.8 | 6.97 dd (8.0, 1.0) | 119.2 | 7.58 t (7.0) | 129.4 | |
| 4′ | 147.6 | 7.50 dt (1.0, 8.0) | 135.4 | 7.62 t (7.0) | 132.3 | |
| 5′ | 6.97 d (8.4) | 115.5 | 7.02 dt (1.0, 8.0) | 120.0 | 7.58 t (7.0) | 129.4 |
| 6′ | 7.40 brd (8.4) | 121.7 | 7.83 dd (8.0, 1.0) | 127.2 | 8.01 d (7.0) | 127.6 |
| 7′ | 169.7e | 169.2 | 164.9 | |||
| 1″a | 4.43 dd (12.0, 3.6) | 62.9 | ||||
| 1″b | 4.33 dd (12.0, 6.0) | |||||
| 2″ | 4.50 m | 78.0 | ||||
| 3″ | 3.69 brd (6.0) | 60.0 | ||||
| OMe | 3.70 s | 55.3 | 3.99 s | 53.2 | 3.96 s | 52.7 |
a
Data were measured in DMSO-d6 for (−)-/(+)-1 (600 MHz for 1H NMR and 150 MHz for 13C NMR) and in Me2CO-d6 for 2 and 3 (500 MHz for 1H NMR and 125 MHz for 13C NMR), respectively. The assignments were based on DEPT, 1H—1H COSY, HSQC, HMQC and HMBC experiments.
b
Data for the hydroxyl group in (−)-/(+)-1: δH 4.98 (1H, brs, OH−3″).
c
Data for the hydroxyl and amino groups in 2: δH 12.22 (1H, brs, OH−5), 11.89 (1H, brs, OH−2′) and 8.65 (1H, brs, NH−2).
d
Data for the hydroxyl and amino groups in 3: δH 11.68 (1H, brs, OH−5) and 8.75 (1H, brs, NH−2).
e
Data in the same column may be exchanged.