Table 1. NMR spectroscopic data for Isororidin A [400 (1H) and 100 MHz (13C), δ ppm]a.
| Position (Scheme 1) | 1H NMR (J in Hz) | 13C NMR | COSY | HMBC | NOESY |
|---|---|---|---|---|---|
| 2 | 3.74 (d, 5.1) | 80.4 | 3b | 4, 5, 12 | 3′, 13a |
| 3 | b: 2.14 (overlap by H-3′) | 35.7 | 2, 4 | 2, 4 | |
| a: 2.47 (dd, 8.2, 15.2) | 2, 5, 12 | ||||
| 4 | 5.84 (dd, 4.5, 8.2) | 76.0 | 3 | 2, 3, 5, 6, 12, 11′ | 11 |
| 5 | Cq | 50.5 | |||
| 6 | Cq | 45.0 | |||
| 7 | 1.87 (m, 2H) | 21.3 | 8 | 6, 8, 9, 11 | 13, 14 |
| 8 | a: 1.93 (d, 8.0) | 28.7 | 7 | 6,7, 9, 10 | |
| b: 1.98 (m) | |||||
| 9 | Cq | 141.7 | |||
| 10 | 5.41 (d, 5.4) | 119.7 | 11, 16 | 6, 8, 11, 16 | |
| 11 | 3.72 (br d, 5.4) | 68.5 | 10 | 7, 10, 15 | 4 |
| 12 | Cq | 66.4 | |||
| 13 | 2.86 (d, 4.0) | 48.5 | 2, 5, 12 | 14 | |
| 3.05 (d, 4.0) | |||||
| 14 | 0.81 (s) | 8.0 | , | 4, 5, 6, 12 | 2′, 3′, 15, 12′ |
| 15 | 4.32 (d, 12.2) | 64.8 | 15 | 5, 6, 7, 1′ | 14 |
| 4.46 (d, 12.2) | 5, 6, 7, 11, 1′ | ||||
| 16 | 1.72 (s) | 23.3 | 10 | 8, 9, 10 | |
| 1′ | CO | 175.6 | |||
| 2′ | 4.04 (d, 4.0) | 76.7 | 3′ | 1′, 4′, 12′ | 14, 3′, 12′ |
| 3′ | 2.08 (m | 37.7 | 2′, 12′ | 1′, 2′ | 14, 2′ |
| 4′ | 1.58 (m) | 34.9 | 4′, 5′ | 3′, 5′, 12′ | |
| 1.73 (m) | 2′, 3′, 5′ | ||||
| 5′ | 3.50 (ddd, 5.2, 8.7, 9.1) | 70.9 | 4′, 5′ | 3′, 4′, 6′ | |
| 3.58 (ddd, 5.2, 9.6, 9.8) | |||||
| 6′ | 3.82 (m) | 84.6 | 7′, 13′ | 5′, 7′, 8′, 14′ | 8′, 14′ |
| 7′ | 6.17 (dd, 3.0, 15.4) | 142.3 | 6′, 8′ | 6′, 8′, 9′ | 13′, 14′ |
| 8′ | 7.60 (ddt, 11.4, 15.4, 1.1) | 126.8 | 7′, 9′ | 6′, 9′, 10′ | 14, 3′, 10′, 12′ |
| 9′ | 6.75 (t, 11.4) | 145.5 | 8′, 10′ | 7′, 8′, 11′ | 7′ |
| 10′ | 5.76 (d, 11.2) | 117.9 | 9′ | 8′, 9′, 11′ | 14 |
| 11′ | CO | 168.1 | |||
| 12′ | 1.09 (d, 6.8) | 15.1 | 3′ | 2′, 3′, 4′ | 14, 2′, 3′, 8′ |
| 13′ | 3.69 (m) | 71.0 | 6′, 14′ | 6′, 14′ | 7′, 8′, 14′ |
| 14′ | 1.16 (d, 6.4) | 18.4 | 13′ | 6′, 13′ | 6′, 7′, 8′,13′ |
Note: (a) the assignments were based on 1H–1H COSY, HSQC–DEPT and HMBC experiments, and recorded in MeOD-d4.