Table 1.
1H and 13C NMR data for the conjugate base (1) and acid (2) forms of hoiamide D (DMSO-d6).
| Compound (1) |
Compound (2) |
|||||
|---|---|---|---|---|---|---|
| Position | δH (J in Hz)a | δ Cb | HMBCa | δH (J in Hz)a | dCb | HMBCa |
| 1 | 179.5 | 176.5 | ||||
| 2 | 1.70, m | 41.6 | 9 | 2.17, dt (6.8, 10.9) | 44.1 | 1, 3, 9 |
| 3 | 3.51, d (10.8) | 71.8 | 1 | 3.81, m | 70.2 | 2 |
| 4 | 3.52, t (10.4) | 53.5 | 1, 5 | 3.53, d (9.6) | 52.7 | 2, 5, 6, 8, 10 |
| 5 | 1.61, m | 36.1 | 1.58, m | 35.5 | 7 | |
| 6a | 1.49, m | 25.4 | 3, 7 | 1.44, m | 25.1 | 7 |
| 6b | 1.04, m | 1.07, m | 5, 7, 8 | |||
| 7 | 0.85, t (7.1) | 11.1 | 6 | 0.84, t (7.2) | 11.0 | 5, 6 |
| 8 | 0.88 d (6.8) | 15.7 | 4, 5 | 0.89, d (6.3) | 15.6 | 4, 5, 6 |
| 9 | 0.85, d (4.1) | 13.8 | 1, 2, 3 | 0.92, d (7.2) | 13.6 | 1, 2, 3 |
| NH | 6.85, d (9.7) | 4, 10 | 6.93, d (9.8) | 10 | ||
| 10 | 173.3 | 173.3 | ||||
| 11 | 84.4 | 84.4 | ||||
| 12a | 3.59, d (11.6) | 40.9 | 10, 11, 13, 14 | 3.61, d (11.3) | 40.6 | 10, 11, 13, 14 |
| 12b | 3.13, d (11.6) | 10, 11, 13, 14 | 3.15, d (11.3) | 10, 11, 13, 14 | ||
| 13 | 1.45, s | 25.7 | 10, 11, 12 | 1.44, s | 25.6 | 10, 11, 12 |
| 14 | 177.7 | 177.6 | ||||
| 15 | 83.6 | 83.7 | ||||
| 16a | 3.74, d (11.4) | 42.2 | 14, 15, 17, 18 | 3.78, d (11.1) | 42.1 | 14, 15, 17, 18 |
| 16b | 3.46, d (11.4) | 14, 15, 17, 18 | 3.45, d (11.1) | 14, 15, 17, 18 | ||
| 17 | 1.57, s | 26.0 | 14, 15, 16 | 1.62, s | 26.0 | 14, 15, 16 |
| 18 | 162.5 | 162.4 | ||||
| 19 | 146.4 | 146.5 | ||||
| 20 | 8.21, d (1.0) | 122.6 | 18, 19, 21 | 8.19, s | 122.5 | 18, 19, 21 |
| 21 | 169.9 | 169.9 | ||||
| 22a | 3.17, m | 33.0 | 21 | 3.16, dd (3.7, 15.3) | 33.1 | 21, 23, 24 |
| 22b | 2.88, dd (10.5, 15.1) | 21, 23 | 2.90, dd (11.0, 15.3) | 21, 23, 24 | ||
| 23 | 3.88, d (10.5) | 80.6 | 21 | 3.86, d (11.0) | 80.5 | 21, 22, 34, 35 |
| 24 | 2.08, m | 35.8 | 34 | 2.09, m | 35.9 | 34 |
| 25 | 3.75, d (10.4) | 69.4 | 24 | 3.74, d (10.0) | 69.7 | 24, 33 |
| 26 | 1.52, m | 37.3 | 1.54, m | 37.3 | 27, 33 | |
| 27 | 3.33, d (7.6) | 72.7 | 26 | 3.33, m | 73.1 | 25, 26, 32 |
| 28 | 1.54, m | 33.7 | 33 | 1.53, m | 33.8 | 27, 32 |
| 29a | 1.32, m | 36.7 | 28 | 1.31, m | 36.6 | 27, 28, 30, 31, 32 |
| 29b | 1.17, m | 28, 30 | 1.18, m | 27, 28, 30, 31, 32 | ||
| 30 | 1.30, m | 19.9 | 1.30, m | 19.9 | 29, 31 | |
| 31 | 0.85, t (7.1) | 14.3 | 30, 32 | 0.86, t (7.3) | 14.3 | 29, 30 |
| 32 | 0.75, d(6.4) | 12.8 | 27, 28 | 0.76, d (6.6) | 12.8 | 28, 29 |
| 33 | 0.71, d (7.1) | 9.0 | 25, 26, 27 | 0.71, d (6.7) | 9.0 | 25, 26, 27 |
| 34 | 0.72, d (7.5) | 9.6 | 23, 24, 25 | 0.73, d (6.6) | 9.6 | 23, 25 |
| 35 | 3.22, s | 56.2 | 23 | 3.21, s | 56.2 | 23 |
| 1-OH | 12.0, s | |||||
| 3-OH | 5.32 brs | 5.29, d (4.7) | 2, 3, 4 | |||
| 26-OH | 4.50, s | 4.27, s | ||||
| 27-OH | 4.23, s | |||||
a
500 and 600 MHz for 1H NMR, HMBC
b
75 MHz for 13C NMR