Table 3. Spectroscopic comparison of natural and synthetic amphidinolide E (1) 1H NMR Data.
| Proton | Natural (Kobayashi, 600 MHz) | Synthetic (Roush, 400 MHz) |
|---|---|---|
| 2 | 3.26 (1H, dq, J = 10.0, 6.8 Hz) | 3.26 (1H, m) |
| 3 | 5.59 (1H, dd, J = 14.0, 10.0) | 5.59 (1H, m) H3, H10 & H23 overlap |
| 4 | 6.20 (1H, dd, J = 14.0, 10.6) | 6.20 (1H, m) H4 and H5 overlap |
| 5 | 6.16 (1H, dd, J = 14.5, 10.6) | 6.16 (1H, m) H4 and H5 overlap |
| 6 | 5.53 (1H, dd, J = 14.5, 8.5) | 5.53 (1H, dd, J = 14.8, 8.8) |
| 7 | 3.88 (1H, t, J = 8.5) | 3.89 (1H, t, J = 8.8) |
| 8 | 3.95 (1H, t, J = 8.5) | 3.95 (1H, t, J = 8.4) |
| 9 | 5.27 (1H, dd, J = 15.6, 8.5) | 5.27 (1H, dd, J = 14.4, 7.6) |
| 10 | 5.64 (1H, m) | 5.64 (1H, m) H3, H10 & H23 overlap |
| 11a | 2.23 (1H, m) | 2.23 (1H, m) |
| 11b | 1.82 (1H, m) | 1.82 (1H, m) |
| 12a | 1.76 (1H, m) | 1.76 (1H, m) |
| 12b | 1.48 (1H, m) | 1.48 (1H, m) |
| 13 | 3.41 (1H, m) | 3.40 (1H, m) |
| 14a | 1.40 (1H, m) | 1.40 (1H, m) |
| 14b | 1.25 (1H, m) | 1.25 (1H, m) |
| 15a | 1.58 (1H, m) | 1.58 (1H, m) overlapping w/water |
| 15b | 1.33 (1H, m) | 1.33 (1H, m) |
| 16 | 3.56 (1H, dt, J = 7.5, 7.1) | 3.56 (1H, m) |
| 17 | 3.72 (1H, dt, J = 7.5, 4.5) | 3.72 (1H, m) |
| 18 | 4.66 (1H, d, J = 8.3) | 4.66 (1H, d, J = 9.2) |
| 19 | 2.25 (1H, m) | 2.25 (1H, m) |
| 20a | 2.40 (1H, d, J = 13.4) | 2.40 (1H, d, J = 14.0) |
| 20b | 1.79 (1H, m) | 1.79 (1H, m) |
| 22 | 6.05 (1H, d, J = 15.9) | 6.05 (1H, d, J = 15.2) |
| 23 | 5.71 (1H, dt, J = 15.9, 6.8) | 5.71 (1H, m) H3, H10 & H23 overlap |
| 24 | 2.78 (2H, br d, J = 6.8) | 2.78 (2H, m) |
| 26a | 4.75 (1H, s) | 4.75 (1H, s) |
| 26b | 4.71 (1H, s) | 4.71 (1H, s) |
| 27 | 1.72 (3H, s) | 1.72 (3H, s) |
| 28a | 4.98 (1H, s) | 4.98 (1H, s) |
| 28b | 4.87 (1H, s) | 4.87 (1H, s) |
| 29 | 0.92 (3H, d, J = 6.6) | 0.92 (3H, d, J = 6.8) |
| 30 | 1.25 (3H, d, J = 6.8) | 1.25 (3H, d, J = 6.8) |