Table 1.
1H and 13C NMR (400/100 MHz, resp.) data of 1, 3, and 9 in CD3OD.
| Unit | Ring | No | 1a | 3b | 9b | |||
|---|---|---|---|---|---|---|---|---|
| 1H (mult., J in Hz) | 13C | 1H (mult., J in Hz) | 13C | 1H (mult., J in Hz) | 13C | |||
| I | C | 2 | 5.03, brs | 77.1 | 100.1 | 100.3 | ||
| 3 | 3.89, dd (2.0, 1.0) | 73.2 | 4.05, d, (3.4) | 68.3 | 4.13, d, (3.5) | 67.8 | ||
| 4 | 4.49, dd (2.0, 0.9) | 37.0 | 4.45, d, (3.4) | 29.5 | 4.20, d, (3.5) | 29.5 | ||
| A | 5 | 157.6* | 157.1 | 156.8 | ||||
| 6 | AB | AB | 6.03, d (2.4) | 98.3 | 5.89, d (2.4) | 98.0 | ||
| 7 | 157.8* | 158.1 | 158.2 | |||||
| 8 | AB | AB | 6.08, d (2.4) | 96.7 | 6.04, d (2.4) | 96.5 | ||
| 9 | 158.1* | 154.2 | 154.0 | |||||
| 10 | 101.7 | 104.4 | 103.9 | |||||
| B | 1′ | 132.7 | 132.6 | 132.4 | ||||
| 2′ | 6.87, d (1.9) | 115.0 | 7.16, d (2.1) | 115.7 | 7.13, d (2.2) | 115.7 | ||
| 3′ | 145.8 | 145.6 | 145.6 | |||||
| 4′ | 145.5 | 146.7 | 146.8 | |||||
| 5′ | 6.71, d (8.2) | 115.7 | 6.82, d (8.4) | 115.6 | 6.80, d (8.4) | 115.6 | ||
| 6′ | 6.71, dd (8.2, 1.9) | 119.1 | 7.03, dd (8.4, 2.1) | 119.8 | 7.01, dd (8.4, 2.2) | 119.9 | ||
| II | F | 2 | 5.31, brs | 79.1 | 4.54, d (9.8) | 84.5 | ||
| 3 | 3.98, brd (1.9) | 72.9 | 4.57, dd (9.8, 8.4) | 73.0 | ||||
| 4 | 4.56, brs | 37.9 | 4.48, brd (8.4) | 38.6 | ||||
| D | 5 | 157.0 | 156.1 | |||||
| 6 | 6.06, s | 96.3 | 5.97, s | 97.6 | ||||
| 7 | 152.4 | 151.9 | ||||||
| 8 | 106.8 | 107.0 | ||||||
| 9 | 152.4 | 152.2 | ||||||
| 10 | 105.6 | 108.8 | ||||||
| E | 1′ | 131.8 | 131.3 | |||||
| 2′ | 7.13, d (2.1) | 116.2 | 7.07, d (2.1) | 116.3 | ||||
| 3′ | 145.9 | 146.2 | ||||||
| 4′ | 146.2 | 146.8 | ||||||
| 5′ | 6.80, d (8.3) | 116.1 | 6.84, d (8.2) | 116.2 | ||||
| 6′ | 6.96, dd (8.3, 2.1) | 120.6 | 6.95, dd (8.2, 2.1) | 121.1 | ||||
| phloroglucinol | 1″ | 107.4 | AB | 107.5 | ||||
| 2″&6″ | 158.7 | AB | 159.7 | |||||
| 3″&5″ | 5.75, s | 95.1 | AB | AB | 5.79, s | 95.5 | ||
| 4″ | 160.0 | AB | 160.1 | |||||
NMR data were acquired at a255 K, and b298 K
interchangeable assignment; AB: absence of signals.