Table 1.
Comparison of NMR data for 1 isolated in the current study (1H-NMR at 600 MHz, 13C-NMR at 150 MHz, basic frequency) with that reported previously for 1 [8–10] and with 3.
| 13C δ (m) | 1H δ (m,JHz) | HMBC (6 Hz) | gHMBC (6 Hz) | 1,1-ADEQUATE | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| No. | 1a,10 | 1a | 3a | 1a,10 | 1a | 1b,9 | 1b | 1c,8 | 1a,10 | 1a | 1a |
| 1 | 163.7 (s) | 163.6 (s) | 163.6 (s) | ||||||||
| 2 | 122.4 (d) | 122.3 (d) | 124.7 (d) | 7.20 (s) | 7.24 (d, 1.4) | 7.17 (brs) | 7.24 (d, 1.4) | 6.73 (d, 1.2) | C-4, 1’ | C-1’, 1, 3, 4, 9a | C-1, 3 |
| 3 | 156.1 (s) | 156.6 (s) | 154.2 (s) | ||||||||
| 4d | 116.6 (d) | 118.4 (d) | 121.2 (d) | 7.70 (s) | 7.72 (d, 1.4) | 7.56 (brs) | 7.66 (d, 1.4) | 7.16 (d, 1.2) | C-2, 10, 1’ | C-1’, 1, 2, 9, 9a, 10 | C-3, 4a |
| 4a | 135.3 (s) | 134.9 (s) | 134.7 (s) | ||||||||
| 5d | 113.6 (d) | 110.4 (d) | 109.1 (d) | 7.09 (s) | 7.16 (d, 2.4) | 6.96 (d, 2.0) | 7.02 (d, 2.5) | 6.61 (d 2.0) | C-10 | C-6, 7, 8, 8a, 9, 10 | C-6, 10a |
| 6d | 160.2 (s) | 166.7 (s) | 166.6 (s) | ||||||||
| 7 | 109.7 (d) | 109.1 (d) | 110.1 (d) | 6.35 (d, 3.4) | 6.52 (d, 2.4) | 6.41 (d 2.0) | 6.44 (d, 2.5) | 6.02 (d, 2.0) | C-5 | C-5, 6, 8, 8a | C-6 |
| 8 | 167.5 (s) | 167.9 (s) | 167.2 (s) | ||||||||
| 8ad | 113.9 (s) | 110.5 (s) | 110.5 (s) | ||||||||
| 9 | 192.0 (s) | 191.7 (s) | 191.9 (s) | ||||||||
| 9ad | 118.4 (s) | 115.9 (s) | 115.0 (s) | ||||||||
| 10 | 184.3 (s) | 183.2 (s) | 183.2 (s) | ||||||||
| 10a | 136.9 (s) | 136.9 (s) | 136.9 (s) | ||||||||
| 1′ | 75.5 (d) | 75.4 (d) | 39.2 (t) | 4.60 (m) | 4.62 (t, 6.4) | 4.56 (m) | 4.57 (t, 6.5) | 4.19 (t, 5.8) | C-2, 4 | C-2’, 3’, 2, 3, 4 | C-2’, 3 |
| 2′ | 32.6 (t) | 32.6 (t) | 24.8 (t) | 1.73 (m) | 1.75 (m) | 1.65 (m) | 1.63 (m) | C-3, 3′ | C-1’, 3’, 3 | C-1’, 3’ | |
| 3′ | 10.3 (q) | 10.2 (q) | 14.0 (q) | 0.94 (t, 12.5) | 0.96 (t, 7.6) | 0.91 (t, 8.0) | 0.86 (t, 7.3) | C-1’, 2′ | C-1’, 2’ | C-2’ | |
a
Measured in CD3OD, referenced to internal solvent signals (δ 3.31 and 49.0 ppm).
b
Measured in DMSO d6, referenced to internal solvent signals (δ2.50).
c
Measured in (CD3)2CO, referenced to TMS (δ0).
d
NMR resonances and coupling constants associated with atoms at these positions are not consistent with the current molecule and the previously reported rhodoptilometrin [10] being identical.