Table 1.
1H-NMR data of compounds 3–7 (400 MHz, δ in ppm, m, J in Hz).
| Position | 3 (in CDCl3) | 4 (in CDCl3) | 5 (in CDCl3) | 6 (in CD3OD) | 7 (in CDCl3) |
|---|---|---|---|---|---|
| 3 | 6.25; d; 9.7; 1H | 6.23; d; 9.5; 1H | 6.24; d; 9.5; 1H | 6.24; d; 9.6; 1H | 6.23; d; 9.6; 1H |
| 4 | 7.63; d; 9.7; 1H | 7.62; d; 9.5; 1H | 7.62; d; 9.5; 1H | 7.88; d; 9.6; 1H | 7.62; d; 9.6; 1H |
| 5 | 7.36; d; 9.2; 1H | 7.34; d; 9.5; 1H | 7.35; d; 8.6; 1H | 7.52; d; 8.6; 1H | 7.34; d; 9.4; 1H |
| 6 | 6.82; dd; 9.2, 2.4; 1H * | 6.82; dd; 9.5, 2.4; 1H * | 6.82; dd; 8.6, 2.4; 1H * | 6.90; dd; 8.6, 2.4; 1H * | 6.82; dd; 9.4, 2.3; 1H * |
| 8 | 6.82; bd; 2.2 1H * | 6.82; bd; 2.1; 1H * | 6.81; bs, 1H * | 6.92; bd, 2.3; 1H * | 6.81; bd; 2.2 1H * |
| 1′α | 2.09; ddd; 3.6, 6.6, 13.2; 1H ** | 1.50; dt; 13.2, 3.3; 1H | 1.45; m; 1H ** | 1.73; m; 1H ** | 1.73; m; 1H ** |
| 1′β | 1.81; dt; 5.5, 13.2; 1H | 1.83; bdt; 3.2, 13.2; 1H | 1.76; m; 1H *** | 1.87; m; 1H *** | 1.84; dt; 2.8, 13.1; 1H |
| 2′α | 2.68; ddd; 6.9, 13.2, 15.1; 1H | 1.67; m; 1H ** | 1.45; m; 1H ** | 1.73; m; 1H ** | 1.73; m; 1H ** |
| 2′β | 2.41; ddd; 3.2, 5.3, 15.1; 1H | 1.67; m; 1H ** | 1.76; m; 1H *** | 1.87; m; 1H ** | 1.73; m; 1H ** |
| 3′ | - | 3.46; bt; 2.6; 1H | 3.30; dd; 4.4, 11.4; 1H | 3.43; bdd; 6.6, 10.0; 1H | 3.79; bt; 2.2; 1H |
| 5′ | 1.67; dd; 2.4, 12.1; 1H | 1.66; dd; 2.4, 12.9; 1H ** | 1.17; dd; 2.7, 12.5; 1H | 1.41; dd; 3.9, 12.6; 1H **** | 1.54; dd; 3.1, 12.3; 1H |
| 6′α | 1.57; m; 1H | 1.42; dq; 4.4, 14.0; 1H | 1.62; m; 1H | 1.41; m; 1H **** | 1.42; dq; 4.3, 13.2; 1H |
| 6′β | 1.73; m; 1H | 1.96; ddt; 2.4, 3.7, 14.0; 1H | 1.76; m; 1H *** | 1.87; m; 1H *** | 1.93; ddt; 2.2, 2.8, 13.2 1H |
| 7′α | 2.53; ddd; 2.3, 4.0, 13.3; 1H | 2.45; ddd; 2.5, 4.2, 13.2; 1H | 2.46; ddd; 2.3, 4.0, 13.2; 1H | 2.46; ddd; 2.3, 3.9, 13.0; 1H | 2.46; ddd; 2.3, 4.1, 13.3; 1H |
| 7′β | 2.14; bdt; 4.8, 13.3; 1H ** | 2.13; bdt; 5.0, 13.2; 1H | 2.09; bdt; 5.1, 13.2; 1H | 2.07; bdt; 5.5, 13.2; 1H | 2.15; bdt; 5.0, 13.3; 1H |
| 9′ | 2.30; bt; 5.4; 1H | 2.33; bdd; 4.2, 7.3; 1H | 2.20; bdd; 4.3, 7.6; 1H | 2.22; bdd; 3.6, 6.9; 1H | 2.34; bdd; 4.5, 6.9; 1H |
| 11′a | 4.24; dd; 6.8, 9.8; 1H *** | 4.23; dd; 4.3, 10.0; 1H | 4.21; dd; 4.3, 9.7; 1H | 4.28; dd; 3.9, 10.3; 1H | 4.22; dd; 4.3, 9.9; 1H |
| 11′b | 4.17; dd; 5.2, 9.8; 1H *** | 4.16; dd; 7.6, 10.0; 1H | 4.17; dd; 7.6, 9.7; 1H | 4.22; dd; 7.7, 10.3; 1H | 4.17; dd; 7.4, 9.9; 1H ** |
| 12′a | 4.97; bs; 1H | 4.90; bd; 1.3; 1H | 4.91; bs; 1H | 4.89; bs; 1H | 4.90; bs; 1H |
| 12′b | 4.60; bs; 1H | 4.53; bd; 1.3; 1H | 4.53; bs; 1H | 4.56; bs; 1H | 4.54; bs; 1H |
| 13′ | 1.12; s; 3H | 0.98; s; 3H | 0.81; s; 3H | 1.23; s; 3H | 1.09; s; 3H |
| 14′a | 1.06; s; 3H | 0.86; s; 3H | 1.02; s; 3H | 4.13; d; 11.1; 1H | 4.18; d; 11.3; 1H ** |
| 14′b | 3.39; d; 11.1; 1H | 3.96; d; 11.3; 1H | |||
| 15′ | 1.04; s; 3H | 0.85; s; 3H | 0.84; s; 3H | 0.85; s; 3H | 0.84; s; 3H |
| OAc | - | - | - | - | 2.04; s; 3H |
*, **, ***, **** Partially overlapped signals.