Table 1.
1H and 13C NMR spectroscopic data for compounds 1, 2, 4–6a (400 and 100 MHz for 1H and 13C NMR, CDCl3).
| Position |
1 |
2 |
4 |
5 |
6 |
|||||
|---|---|---|---|---|---|---|---|---|---|---|
| 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) | |
| 2 | 152.3 | 8.02, s | 152.5 | 8.01, s | 154.5 | 8.05, s | 155.4 | 7.97, s | 155.2 | 7.94, s |
| 3 | 123.9 | 124.1 | 120.9 | 119.8 | 119.9 | |||||
| 4 | 176.1 | 175.9 | 176.0 | 181.8 | 181.4 | |||||
| 4a | 120.7 | 120.7 | 120.8 | 108.6 | 105.8 | |||||
| 5 | 103.8 | 7.60, s | 103.9 | 7.59, s | 103.9 | 7.59, s | 152.5 | 160.9 | ||
| 6 | 151.1 | 151.2 | 151.0 | 136.6 | 95.1 | 6.41, s | ||||
| 7 | 151.9 | 151.9 | 151.8 | 157.1 | 162.7 | |||||
| 8 | 124.7 | 124.7 | 124.7 | 113.0 | 107.8 | |||||
| 8a | 150.0 | 149.9 | 149.9 | 150.4 | 154.6 | |||||
| 1′ | 124.5 | 125.9 | 112.5 | 110.0 | 109.9 | |||||
| 2′ | 130.1 | 7.52, d (8.8) | 122.3 | 7.00, dd (8.0, 1.6) | 151.9 | 152.4 | 152.5 | |||
| 3′ | 113.9 | 6.98, d (8.8) | 108.4 | 6.87, d (8.0) | 98.3 | 6.63, s | 100.0 | 6.67, s | 100.0 | 6.66, s |
| 4′ | 159.5 | 147.6 | 149.8 | 146.9 | 146.8 | |||||
| 5′ | 113.9 | 6.98, d (8.8) | 147.6 | 143.1 | 140.4 | 140.4 | ||||
| 6′ | 130.1 | 7.52, d (8.8) | 109.8 | 7.12, d (1.6) | 115.3 | 6.96, s | 114.4 | 6.87, s | 114.4 | 6.88, s |
| 7′ | 101.1 | 5.99, s | ||||||||
| 1″ | 22.9 | 3.59, d (7.2) | 22.9 | 3.59, d (7.2) | 23.0 | 3.60, d (7.2) | 22.2 | 3.46, d (7.2) | 21.5 | 3.42, d (7.2) |
| 2″ | 121.5 | 5.21, t (7.2) | 121.5 | 5.21, t (7.2) | 121.6 | 5.23, t (7.2) | 122.2 | 5.18, t (7.2) | 122.1 | 5.17, t (7.2) |
| 3″ | 132.7 | 132.7 | 132.6 | 132.1 | 131.9 | |||||
| 4″ | 17.9 | 1.84, s | 17.9 | 1.84, s | 17.9 | 1.84, s | 17.8 | 1.81, s | 17.8 | 1.79, s |
| 5″ | 25.8 | 1.69, s | 25.8 | 1.69, s | 25.8 | 1.70, s | 25.8 | 1.70, s | 25.8 | 1.68, s |
| 6-OCH3 | 56.0 | 3.96, s | 56.1 | 3.96, s | 56.0 | 3.96, s | 60.7 | 3.93, s | ||
| 7-OCH3 | 61.1 | 3.93, s | 61.1 | 3.93, s | 61.1 | 3.93, s | 61.4 | 4.01, s | 56.1 | 3.90, s |
| 2′-OCH3 | 56.9 | 3.79, s | 56.5 | 3.74, s | 56.5 | 3.75, s | ||||
| 4′-OCH3 | 55.3 | 3.84, s | 56.2 | 3.94, s | ||||||
| 5′-OCH3 | 56.6 | 3.86, s | 56.7 | 3.86, s | 56.7 | 3.86, s | ||||
a
Chemical shifts are given in ppm. J values (Hz) are given in parentheses. Assignments were made based on the analysis of 1H–1H COSY, HSQC, and HMBC data.