Table 1.
NMR data for lophocladine A (1) and B (2) in d6-DMSO (δ in ppm, J in Hz).
| 1 | 2 | |||||
|---|---|---|---|---|---|---|
| position | δHa | δCb | HMBCc,d | 1JC,Hc | δHa | δCb |
| 1 | 160.9 qC | 157.5 qC | ||||
| N-2 | 11.80 (1H, brs) | |||||
| 3 | 7.39 (1H, d, J = 2.5) | 133.0 CH | 1, 4, 4a, 5, 8a, 1′ | 179.1 | 7.98 (1H, s) | 146.3 CH |
| 4 | 115.7 qC | 111.8 qC | ||||
| 4a | 141.9 qC | 138.2 qC | ||||
| 5 | 7.39 (1H, d, J = 5.6) | 117.3 CH | 1, 4, 4a, 6, 8, 8a | 165.1 | 7.51 (1H, d, J = 5.9) | 116.4 CH |
| 6 | 8.71 (1H, d, J = 5.6) | 151.2 CH | 4, 4a, 5, 8 | 180.2 | 8.57 (1H, d, J = 5.9) | 147.5 CH |
| N-7 | ||||||
| 8 | 9.40 (1H, s) | 150.4 CH | 1, 4a, 6, 8a | 180.2 | 9.59 (1H, s) | 149.2 CH |
| 8a | 120.6 qC | 120.1 qC | ||||
| 1′ | 134.8 qC | 136.5 qC | ||||
| 2′ | 7.51 (1H, m) | 128.8 CH | 4, 1′, 3′, 4′, 5′, 6′ | 160.7 | 7.49 (1H, m) | 128.7 CH |
| 3′ | 7.45 (1H, m) | 129.6 CH | 4, 2′, 4′, 5′, 6′ | 161.4 | 7.44 (1H, m) | 129.6 CH |
| 4′ | 7.44 (1H, m) | 127.7 CH | 2′,3′,5′,6′ | 158.7 | 7.42 (1H, m) | 127.1 CH |
| 5′ | 7.45 (1H, m) | 129.6 CH | 4, 2′, 3′, 4′, 6′ | 161.4 | 7.44 (1H, m) | 129.6 CH |
| 6′ | 7.51 (1H, m) | 128.8 CH | 4, 1′, 2′, 3′, 4′, 5′ | 160.7 | 7.49 (1H, m) | 128.7 CH |
a
Recorded at 300 MHz.
b
Recorded at 75 MHz, multiplicity determined by DEPT.
c
Obtained through 1D- and 2D-HMBC experiments (100 MHz) employing various delay times (42, 65 and 125 ms).
d
Protons showing long range correlation with indicated carbon.