Table 1. NMR Spectroscopic Data for Marinoterpins A–C (1–3) (CD3OD, 500 MHz).
| marinoterpin
A (1) |
marinoterpin
B (2) |
marinoterpin
C (3) |
||||
|---|---|---|---|---|---|---|
| no. | δH mult (J, Hz) | δC | δH mult (J, Hz) | δC | δH mult (J, Hz) | δC |
| 2 | 147.6 | 149.6 | 163.1 | |||
| 3 | 135.5 | 134.4 | 138.3 | |||
| 4 | 8.48, s | 129.5 | 7.89, s | 129.2 | 7.67, s | 135.5 |
| 4a | 128.9 | 129.8 | 121.3 | |||
| 5 | 8.16, dd (8.2, 1.3) | 130.8 | 7.97, d (8) | 129.3 | 7.64, d (8) | 128.2 |
| 6 | 7.79, br t (7.7) | 130.2 | 7.69, t (7.5) | 129.5 | 7.29, t (7.5) | 122.6 |
| 7 | 7.97, br t (7.9) | 134.2 | 7.82, t (8) | 131.7 | 7.60, t (8) | 129.8 |
| 8 | 8.66, d (8.8) | 120.0 | 8.60, d (9) | 119.7 | 7.55, d (8) | 114.4 |
| 8a | 142.4 | 138.5 | 138.5 | |||
| 9 | 2.78, s | 16.1 | 2.73, s | 15.0 | 4.55, m | 77.1 |
| 1′ | 202.9 | 3.61, d (7) | 33.1 | 3.33, d (7) | 28.9 | |
| 2′ | 3.12, dd (16.9, 5.8) | 49.8 | 5.33, t (7) | 122.1 | 5.41, t (7) | 121.2 |
| 2.97, dd (16.9, 7.6) | ||||||
| 3′ | 2.17, ma | 30.3 | 139.4 | 138.2 | ||
| 4′ | 1.51, m/1.37, m | 37.4 | 2.18, ma | 40.2 | 2.19, ma | 39.1 |
| 5′ | 1.99 | 27.8 | 2.11, ma | 28.7 | 2.13, ma | 27.7 |
| 6′ | 5.33, ma | 121.3 | 5.32, ma | 121.0 | 5.37, ma | 129.6 |
| 7′ | 140.1 | 140.2 | 138.8 | |||
| 8′ | 2.59, dd (15.2, 5.8)b/2.18, ma | 40.3 | 2.58, dd (15, 5.5)/2.18, ma | 40.3 | 2.58, dd (15, 5.5)/2.18, ma | 39.1 |
| 9′ | 4.57, ma | 77.5 | 4.55, ma | 77.5 | 4.55, ma | 76.3 |
| 10′ | 5.19, d (8.5)b | 126.2 | 5.18, ma | 126.3 | 5.19, ma | 124.8 |
| 11′ | 140.7 | 140.7 | 139.6 | |||
| 12′ | 2.04, ma | 40.0 | 2.06, ma | 40.0 | 2.06, ma | 38.5 |
| 13′ | 2.02, ma | 28.6 | 2.05, ma | 28.6 | 2.05, ma | 28.9 |
| 14′ | 5.31, ma | 120.8 | 5.29, ma | 120.8 | 5.30, ma | 120.1 |
| 15′ | 140.2 | 140.2 | 137.1 | |||
| 16′ | 2.59, dd (15.2,5.8)b/2.18,ma | 40.2 | 2.58, dd (15, 5.5) /2.18, ma | 40.3 | 2.58, dd (15, 5.5) | 39.5 |
| 17′ | 4.57, ma | 77.4 | 4.55, ma | 77.4 | 4.55, ma | 76.1 |
| 18′ | 5.19, d (8.5)b | 125.9 | 5.18, ma | 125.9 | 5.18, ma | 125.2 |
| 19′ | 138.0 | 138.0 | 139.6 | |||
| 20′ | 1.73, s | 25.9 | 1.72, s | 25.9 | 1.73, s | 24.8 |
| 21′ | 1.03, d (6.6) | 20.1 | 1.79, s | 16.4 | 1.61, s | 16.1 |
| 22′ | 4.39, t (14.3)b/4.23, ma | 69.0 | 4.21, d (13)/4.38, t (12.5) | 69.0 | 4.21, d (13)/4.39, t (12.5) | 67.9 |
| 23′ | 1.70, ma | 16.7 | 1.67, s | 16.7 | 1.73, s | 15.1 |
| 24′ | 4.39, t (14.3)b/4.23, ma | 69.0 | 4.21, d (13)/4.38, t (12.5) | 69.0 | 4.21, d (13) /4.39, t (12.5) | 67.9 |
| 25′ | 1.70, ma | 18.3 | 1.69, s | 18.3 | 1.71, s | 15.5 |
a
Coupling constants were not determined due to overlapping signals.
b
The coupling constant was derived from 2D homo-J-resolved 1H NMR spectral data.