Table 3. NMR data for tamanolide E1, tamanolide E2, calanolide D, inophyllum E at 500 MHz (CDCl3, 300 K).
| Atom | Tamanolide-E1 (diast-1/2 70/30) | Tamanolide-E2 (diast 1/2 40/60) | Tamanolide D | Inophyllum-E | ||
|---|---|---|---|---|---|---|
| δ13C | δ1Η | δ13C | δ1Η | δ1Η | δ1Η | |
| 2 | 160.4 (C) | – | 160.4 (C) | – | – | – |
| 3 | 109.3 (CH) | 6.16 (brs) | 109.3 (CH) | 6.16 (brs) | 6.08 (brs) | 6.05 (s) |
| 4 | 163.0 (C) | – | 163.0 (C) | – | – | – |
| 4a | 104.7 (C) | – | 104.7 (C) | – | – | – |
| 4b | 156.2 (C) | – | 156.2 (C) | – | – | – |
| 6 | 79.4 (C) | – | 79.4 (C) | – | – | – |
| 7 | 127.2 (CH) | 5.60 (d, 10.0) | 127.2 (CH) | 5.60 (d, 10.0) | 5.54 (d, 10.0) | 5.41 (d, 10.0) |
| 8 | 116.1 (CH) | 6.66 (d, 10.0) | 116.1 (CH) | 6.66 (d, 10.0) | 6.66 (d, 10.0) | 6.55 (d, 10.0) |
| 8a | 105.9 (C) | – | 105.9 (C) | – | – | – |
| 8b | 158.9 (C) | – | 158.9 (C) | – | – | – |
| 10 | 77.4 (CH) | 4.69 (qd, 6.6, 3.4) | 77.4 (CH) | 4.70 (qd, 6.6, 3.4) | 4.51 (qd, 6.6, 1.8) | 4.72 (qd, 6.6, 3.4) |
| 11 | 46.2 (CH) | 2.68 (qd, 7.2,3.4) | 46.1 (CH) | 2.69 (qd, 7.2, 3.4) | 2.03 (qdd, 7.2, 2.1; 1.8) | 2.71 (qd, 7.2, 3.4) |
| 12 | 191.7 (C) | – | 191.6 (C) | – | – | – |
| 12a | 103.2 (C) | – | 103.2 (C) | – | – | – |
| 12b | 155.9 (C) | – | 155.9 (C) | – | – | – |
| 13 | 37.5 (CH) | 3.79 (brsxt, 7.0) | 37.5 (CH) | 3.79 (brsxt, 7.0) | 3.86 (brsxt; 6.6) | – |
| 14 | 29.5 (CH2) | 1.75 (m) | 29.6 (CH2) | 1.75 (m) | 1.78 (m) | 7.37 (m) |
| 1.45 (m) | 1.45 (m) | 1.46 (m) | ||||
| 15 | 12.0 (CH3) | 0.95 (t, 7.4) | 12.0 (CH3) | 0.96 (t, 7.4) | 0.97 (t, 7.3) | 7.22 (m) |
| 16 | 20.1 (CH3) | 1.22 (d, 6.7) | 20.0 (CH3) | 1.22 (d, 6.7) | 1.22 (d, 6.9) | 7.37 (m) |
| 17 | – | – | – | – | – | 7.22 (m) |
| 18 | – | – | – | – | – | 7.37 (m) |
| 19 | 28.3 (CH3) | 1.54 (s) | 28.3 (CH3) | 1.53 (s) | 1.48 (s) | 0.97 (s) |
| 20 | 28.2 (CH3) | 1.53 (s) | 28.2 (CH3) | 1.53 (s) | 1.49 (s) | 0.95 (s) |
| 21 | 16.2 (CH3) | 1.42 (d, 6.6) | 16.2 (CH3) | 1.41 (d, 6.6) | 1.43 (d, 6.6) | 1.42 (d, 6.6) |
| 22 | 9.4 (CH3) | 1.15 (d, 7.2) | 9.4 (CH3) | 1.15 (d, 7.2) | 0.80 (d, 7.2) | 1.18 (d, 7.3) |
Note:
δ in ppm, (13C multiplicity determinate by 13C-DEPTQ135 and HSQCed), (br, broad; s, singlet; d, doublet; t, triplet; q,quadruplet; sxt, sextuplet; m, multiplet; J Hz).