Table 2.
NMR Data of Compounds 3 and 4 a.
| Position | 3 | 3 b | 4 | |||
|---|---|---|---|---|---|---|
| δC Mult | δH (J in Hz) | δC Mult | δH (J in Hz) | δC Mult | δH (J in Hz) | |
| 1 | 55.8, CH | 4.80, m | 54.6 | 5.01, br, s | 55.2, CH | 4.72, m |
| 2 | - | - | - | - | - | - |
| 3 | 60.2, CH | 3.86, m | 59.7 | 4.26, br, d (7.3) | 60.6, CH | 3.70, m |
| 4 | 25.0, CH2 | 3.30, dd (15.3, 4.0) | 24.2 | 3.36, m | 25.7, CH2 | 3.28, dd (15.4, 3.8) |
| - | 2.90, dd (15.3, 13.6) | - | 3.04, dd (15.1, 12.4) | - | 2.96, dd (15.4, 13.8) | |
| 4a | 108.5, qC | - | 107.9 | - | 109.3, qC | - |
| 4b | 128.7, qC | - | 128 | - | 129.1, qC | - |
| 5 | 103.8, CH | 6.82, d (2.1) | 103.4 | 6.86, d (2.3) | 103.8, CH | 6.84, d (2.4) |
| 6 | 152.4, qC | - | 152.2 | - | 152.4, qH | - |
| 7 | 113.7, CH | 6.68, dd (8.7, 2.1) | 113.8 | 6.75, dd (8.7, 2.3) | 113.5, CH | 6.67, dd (8.7, 2.4) |
| 8 | 113.3, CH | 7.17, d (8.7) | 113.1 | 7.22, d (8.7) | 113.2, CH | 7.17, d (8.7) |
| 8a | 133.7, qC | - | 133.4 | - | 133.8, qC | - |
| 9 | - | - | - | - | - | - |
| 9a | 131.6, qC | - | 129.7 | - | 130.7, qC | - |
| 10 | 31.0, CH2 | 3.48, m | 28.8 | 3.73, br, d (14.2) | 28.4, CH2 | 3.64, m |
| - | 3.18, m | - | 3.36, m | - | 3.24, m | |
| 11 | 136.0, qC | - | 130.7 | - | 130.7, qC | - |
| 12 | - | - | - | - | - | - |
| 13 | 137.7, CH | 7.68, s | 136.2 | 8.73, s | 141.0, CH | 7.69, s |
| 14 | - | - | - | - | - | - |
| 15 | 117.2, CH | 7.00, s | 118.6 | 7.27, s | 134.6, qC | - |
| COOH | 174.9, qC | - | 170.6 | - | 176.0, qC | - |
| NCH3 | - | - | - | - | 33.3, CH3 | 3.71, s |
| SCH3 | - | - | - | - | 19.8, CH3 | 2.39, s |
a NMR data were measured in CD3OD on a Bruker DRX 400 MHz spectrometer; chemical shifts (ppm) are referenced to CD3OD (δ 3.33 ppm, 49.5 ppm). Proton coupling constants (J) in Hz are given in parentheses. The assignments were based on DEPT, 1H-1H COSY, HMQC, and HMBC experiments; b NMR data were reported in the literature [29]. Chemical shifts (ppm) are referenced to CD3OD (δ 3.30 ppm, 49.0 ppm).