Table 2.
Characteristic 1H and 13C NMR Data for Compounds 5–7 (CDCl3, 400 and 100 MHz, Respectively)a
| paynantheine (5) | isopaynantheine (6) | epiallo-isopaynantheine (7) | |||||||
|---|---|---|---|---|---|---|---|---|---|
| Position | δC | type | δH (J in Hz) | δC | type | δH (J in Hz) | δC | type | δH (J in Hz) |
| 3 | 60.1 | CH | 3.20, m | 53.8 | CH | 4.73, bs | 53.9 | CH | 4.85, bs |
| 10 | 99.9 | CH | 6.45, d (7.8) | 99.7 | CH | 6.49, d (7.6) | 99.7 | CH | 6.49, d (7.8) |
| 11 | 122.1 | CH | 7.00, t (7.9) | 122.6 | CH | 7.07, t (7.9) | 122.9 | CH | 7.08, t (7.9) |
| 12 | 104.3 | CH | 6.88, d (8.0) | 105.0 | CH | 7.02, d (8.1) | 105.0 | CH | 7.01, d (8.1) |
| 17 | 160.0 | CH | 7.33, s | 160.2 | CH | 7.28, s | 160.3 | CH | 7.28, s |
| 18 | 115.7 | CH2 | 5.01, dd (17.3, 2.0) 4.96, dd (10.4, 2.1) |
116.7 | CH2 | 4.96, dd (17.2, 1.8) 4.89, dd (10.2, 1.8) |
117.2 | CH2 | 4.98, dd (17.3, 1.7) 4.91, dd (10.3, 1.8) |
| 19 | 139.4 | CH | 5.55, dt (17.9, 9.3) | 137.9 | CH | 5.29, ddd (18.0, 10.3, 8.3) | 137.1 | CH | 5.27, ddd (18.0, 10.3, 8.3) |
| 9-OCH3 | 55.4 | CH3 | 3.88, s | 55.3 | CH3 | 3.89, s | 55.3 | CH3 | 3.88, s |
| 17-OCH3 | 61.7 | CH3 | 3.78, s | 61.7 | CH3 | 3.76, s | 61.7 | CH3 | 3.76, s |
| 22-OCH3 | 51.5 | CH3 | 3.69, s | 51.4 | CH3 | 3.67, s | 51.5 | CH3 | 3.67, s |
| NH | 7.85, s | 8.91, s | 9.12, s | ||||||
a
See Table S5 for a full comparison for the 1H and 13C NMR data for 5–7 (Supporting Information).