Table 1.
NMR Spectroscopic Data (1H 600 MHz, 13C 150 MHz, CDCl3) for 1–3
| anaephene A (1) | anaephene B (2) | anaephene C (3) | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| No | δC, Type | δH (J in Hz) | HMBC | COSY | δC, Type | δH (J in Hz) | HMBC | COSY | δC, Type | δH (J in Hz) | HMBC | COSY | ||
| 1 | 155. 6, C | 155.6, C | 155.6, C | |||||||||||
| 2 | 115.4, CH | 6.65, br s | 1, 3, 4 6, 1’ | 115.4, CH | 6.65, br s | 1, 3, 4 6, 1’ | 115.5, CH | 6.66, br s | 1, 3, 4 6, 1’ | |||||
| 3 | 145.0, C | 144.9, C | 144.0, C | |||||||||||
| 4 | 121.1, CH | 6.75, d (7.7) | 1, 2, 3 5, 6, 1’ | 5 | 121.1, CH | 6.75, d (7.7) | 1, 2, 3 5, 6, 1’ | 5 | 121.1, CH | 6.76, d (7.7) | 1, 2, 3 5, 6, 1’ | 5 | ||
| 5 | 129.5, CH | 7.13, t (7.7) | 1, 3, 4 6 | 4, 6 | 129.6, CH | 7.14, t (7.7) | 1, 3, 4 6 | 4, 6 | 129.6, CH | 7.14, t (7.7) | 1, 3, 4 6 | 4, 6 | ||
| 6 | 112.6, CH | 6.63, m | 1, 2, 4 | 5 | 112.7, CH | 6.64, d (2.6) | 1, 2, 4 | 5 | 112.9, CH | 6.64, d (2.6) | 1, 2, 4 | 5 | ||
| 1’ | 35.8, CH2 | 2.55, t (7.7) | 2, 3, 4 2’ | 2’ | 35.8, CH2 | 2.56, t (7.7) | 2, 3, 4 2’ | 2’ | 35.9, CH2 | 2.65, t (7.6) | 2, 3, 4 | 2’ | ||
| 2’ | 30.9, CH2 | 1.60, m | 3, 1’, 3’ 4’ | 1’, 3’ | 30.8, CH2 | 1.60, m | 3, 1’, 3’ 4’ | 1’, 3’ | 34.4, CH2 | 2.36, m | 1’, 3’,4’ | 1’, 3’ | ||
| 3’ | 29.4, CH2 | 1.38, m | 2’, 4’, 5’ | 2’, 4’ | 29.2, CH2 | 1.39, m | 1’, 5’ | 2’, 4’ | 131.0, CH | 5.59, m | 1’, 2’ | 4’ | ||
| 4’ | 32.6, CH2 | 2.01, m | 3’, 5’, 6’ | 3’ | 32.5, CH2 | 2.01, m | 3’, 5’ | 3’, 5’ | 131.1, CH | 6.04, m | 3’, 5’ | 3’ | ||
| 5’ | 130.3, CH | 5.38, m | 4’, 6’ | 6’ | 131.4, CH | 5.43, dt (15.5, 6.7) | 4’, 6’ | 130.4, CH | 5.99, m | 6’ | ||||
| 6’ | 130.6, CH | 5.40, m | 5’,7’ | 5’, 7’ | 129.4, CH | 5.36, dt (15.5, 6.7) | 8’ | 5’, 7’ | 133.0, CH | 5.57, m | 5’ | |||
| 7’ | 34.9, CH2 | 1.95, m | 6’, 8’, 9’ | 6’, 8’ | 31.6, CH2 | 2.09, m | 6’, 8’, 9’ | 6,’8’ | 34.8, CH2 | 2.03, m | 6’, 9’ | 8’ | ||
| 8’ | 22.9, CH2 | 1.34, m | 6’, 9’ | 7’, 9’ | 28.5, CH2 | 1.58, m | 10’ | 7’, 9’ | 26.6, CH2 | 1.40, m | 6’, 7’, 9’ | 7’, 9’ | ||
| 9’ | 13.8, CH3 | 0.88, t (7.4) | 7’, 8’ | 8’ | 17.9, CH2 | 2.18, m | 11’ | 11’ | 13.9, CH3 | 0.90, t (7.4) | 8’ | 8’ | ||
| 10’ | 87.6, C | |||||||||||||
| 11’ | 68.4, CH | 1.95, t (2.6) | 9’ | |||||||||||
| 1-OH | 4.79, br s | 4.66, s | 1, 2, 6 | 4.66, s | 1, 2, 6 | |||||||||