Table 2.
1H and 13C NMR spectral data of harziaphilic acid (9).
| Position | 9 (DMSO-d 6). 50 °C | 9- d 4 (CD3OD) | ||||
|---|---|---|---|---|---|---|
| δC (mult.) | δH (J in Hz) | HMBCa | ROESY | δC (mult.) | δH (J in Hz) | |
| 2 | 170.1 (C) | — | — | — | 173.6 (C) | — |
| 3 | 43.5 (CH2) | 2.49 (d, 17.1) | 2, 4, 5 | — | 44.3b | — |
| 2.42 (d, 17.1) | 2, 4 | — | ||||
| 4 | 107.1 (C) | — | — | — | 108.7 (C) | — |
| 5 | 69.8 (CH) | 3.79 (dd, 7.5, 3.1) | 2, 4, 7 | 6a, 6b, 11 | 71.6 (CH) | 3.98 (dd, 7.6, 3.1) |
| 6 | 34.4 (CH2) | 2.44 (dd, 14.0, 7.5) | 12 | 5, 6b | 2.68 (dd, 14.5, 7.6) | |
| 1.81 (dd, 14.0, 3.1) | 4, 5, 7, 8, 12 | 5, 6a, 8, 9, 10, 11 | 35.1 (CH2) | 2.05 (dd, 14.5, 3.1) | ||
| 7 | 91.2 (C) | — | — | — | 93.2 (C) | — |
| 8 | 33.2 (CH) | 2.03 (septet, 6.8) | 7, 9, 10, 12 | 6b, 9, 10 | 35.1 (CH) | 2.12 (septet, 6.9) |
| 9 | 17.5 (CH3) | 0.82 (d, 6.8) | 7, 8, 10 | 6b, 8 | 17.8 (CH3) | 0.91 (d, 6.9) |
| 10 | 16.6 (CH3) | 0.75 (d, 6.8) | 7, 8, 9 | 6b, 8 | 17.0 (CH3) | 0.85 (d, 6.9) |
| 11 | 26.7 (CH3) | 2.66 (s) | 2, 5 | 5, 6b | 27.7 (CH3) | 2.81 (s) |
| 12 | 176.4 (C) | — | — | — | 179.5 (C) | — |
Abbreviations: s, singlet; d, doublet; dd, doublet of doublets.
aHMBC correlations, optimized for 8.3 Hz, are from proton stated to the indicated carbon.
bδC determined from the HMBC experiment.