Table 1.
1H- and 13C-NMR spectral data of chlidanthine (1), δ in ppm, J in Hz.
| Position | 1H * (J, Hz) | NOESY | 13C ** | HMBC *** |
|---|---|---|---|---|
| 1 | 4.50 (td, J = 3.3, 1.2) | H(2α), H(2β), H(11α) | 87.2 s | C(11) |
| 2α | 1.99 (ddd, J = −15.9, 5.8, 3.3) | H(1), H(3) | 28.1 t | |
| 2β | 2.59 (ddd, J = −15.9, 3.3, 1.5) | H(1) | ||
| 3 | 3.79 (m, J = 5.8, 1.5) | H(2α) | 70.0 s | C(4), C(1), OMe |
| 4 | 5.98 (ddd, J = 10.4, 4.5, 1.2) | H(4a) | 124.3 s | C(2), C(10b) |
| 4a | 6.17 (dt, J = 10.4, 1.2) | H(4), H(6β), H(12β) | 129.4 s | C(1), C(3), C(10b) |
| 6α | 3.62 (d, J = −15.0) | H(7), H(12α), NMe | 60.6 t | C(10a), C(6a), C(7), C(12), NMe |
| 6β | 4.09 (d, J = −15.0) | H(4a), H(12β) | C(10a), C(6a), C(7), C(12), NMe | |
| 6a | 128.7 s | |||
| 7 | 6.47 (d, J = 8.0) | H(6α), H(8) | 121.9 d | C(10), C(10ª), C(6) |
| 8 | 6.60 (d, 8.0) | H(7) | 115.3 d | C(9), C(10), C(6a) |
| 9 | 145.4 s | |||
| 10 | 140.1 s | |||
| 10a | 132.1 s | |||
| 10b | 48.6 s | |||
| 11α | 2.10 (dt, J = −13.3, 3.0) | H(1) | 34.6 t | C(10b) |
| 11β | 1.52 (ddd, J = −13.3, 3.8, 1.6) | H(12α) | ||
| 12α | 3.03 (d, J = −14.3) | H(6α), H(11β), NMe | 54.0 t | |
| 12β | 3.28 (d, J = −14.3, 1.4) | H(4a), H(6β) | ||
| OMe | 3.37 s | 56.8 q | C(3) | |
| NMe | 2.36 s | H(6α), H(11α), H(12α) | 41.9 q | C(6), C(12) |
* 500 MHz/CDCl3; ** 125 MHz/CDCl3; *** 3J & 4J.