Table 1.
1H- and 13C-NMR spectral data of compounds 6, 7 and 8 [(600/150 MHz, in DMSO-d 6, 25 °C, TMS, δ (ppm) (J = Hz)]
Position | 6 | 7 | 8 | |||
---|---|---|---|---|---|---|
δ H | δ C | δ H | δ C | δ H | δ C | |
2 | – | 164.1 | – | 164.0 | – | 163.9 |
3 | 7.07 (s) | 103.7 | 7.06 (s) | 103.9 | 6.96 (s) | 103.3 |
4 | – | 182.0 | – | 181.8 | – | 181.9 |
4a | – | 105.4 | – | 105.5 | – | 105.3 |
5 | – | 161.0 | – | 161.2 | – | 161.1 |
6 | 6.52 (d 2.0) | 99.4 | 6.49 (br s) | 99.4 | 6.52 (d 1.9) | 99.3 |
7 | – | 162.5 | – | 162.7 | – | 162.6 |
8 | 7.01 (d 2.0) | 95.7 | 6.86 (br s) | 95.2 | 6.85 (d 1.9) | 95.1 |
8a | – | 156.7 | – | 156.9 | – | 156.6 |
1′ | – | 120.1 | – | 120.2 | – | 119.8 |
2′ | 7.37 (s) | 104.7 | 7.37 (s) | 104.6 | 7.28 (s) | 104.3 |
3′ | – | 148.1 | – | 148.2 | – | 148.0 |
4′ | – | 140.0 | – | 140.0 | – | 140.1 |
5′ | – | 148.1 | – | 148.2 | – | 148.0 |
6′ | 7.37 (s) | 104.7 | 7.37 (s) | 104.6 | 7.28 (s) | 104.3 |
3′,5′-OMe | 3.89 (s) | 56.3 | 3.89 (s) | 56.4 | 3.88 (s) | 56.2 |
5-OH | 12.97 (br s) | – | 13.05 (br s) | – | 13.01 (br s) | – |
1′′ | 5.33 (d 5.7) | 98.3 | 5.10 (d 7.4) | 99.7 | 5.15 (d 7.3) | 99.5 |
2′′ | 3.55 (m) | 82.5 | 3.30 (m) | 73.0 | 3.32 (m) | 72.9 |
3′′ | 3.19 (m) | 77.0 | 3.32 (m) | 76.1 | 3.37 (m) | 76.2 |
4′′ | 3.44 (m) | 70.9 | 3.17 (m) | 69.6 | 3.26 (m) | 70.0 |
5′′ | 3.98 (m) | 74.6 | 3.75 (m) | 73.8 | 3.82 (m) | 73.7 |
6′′ | – | 170.0 | 4.34 (d 11.6) | 63.8 | 4.57 (d 11.9) | 63.2 |
4.15 (dd 11.9, 6.5) | 4.10 (dd 11.9, 7.3) | |||||
1′′′ | 4.48 (d 7.9) | 104.7 | – | 167.4 | – | 124.1 |
2′′′ | 2.99 (m) | 74.6 | 3.27 (s) | 42.3 | 6.80 (s) | 105.7 |
3′′′ | 3.16 (m) | 76.1 | – | 167.7 | – | 147.8 |
4′′′ | 3.10 (m) | 69.6 | – | – | – | 138.1 |
5′′′ | 3.55 (m) | 75.0 | – | – | – | 147.8 |
6′′′ | 3.53 (m) | 60.6 | – | – | 6.80 (s) | 105.7 |
3.44 (m) | ||||||
7′′′ | – | – | – | – | 7.47 (d 15.9) | 145.4 |
8′′′ | – | – | – | – | 6.44 (d 15.9) | 114.3 |
9′′′ | – | – | – | – | – | 166.2 |
3′′′,5′′′-OMe | – | – | – | – | 3.71 (s) | 55.7 |
s Singlet, m multilet, d doublet, dd double doublet, br s broad singlet