Table 1.
1H NMR (500 MHz) data of compounds 1–5 (δ in ppm, J in Hz).
| Position | 1 a | 2 b | 3 b | 4 b | 5 c |
|---|---|---|---|---|---|
| 3α | 2.38, m (overlap) | 2.89, d (16.0) | 2.48, m (overlap) | 2.28, m (overlap) | 2.63, m (overlap) |
| 3β | 2.32, m (overlap) | 3.08, d (16.0) | 2.08, t (12.7) | 2.22, m (overlap) | 3.07, d (13.8) |
| 4 | 3.30, dd (8.7, 8.0) | 2.30, m | 2.96, t (8.0) | 3.14, t (8.6) | |
| 5 | 5.93, d (2.3) | 4.08, d (8.8) | |||
| 6 | 2.42, m (overlap) | 5.89, dd (9.6, 2.3) | 5.55,d (10.0) | α 2.77, dd (13.3, 7.3) β 2.27, m (overlap) | 2.33, m (overlap) |
| 7 | α 2.40, m (overlap) β 1.84, td (12.2, 6.2) | 5.59, d (9.6) | 5.69, d (10.0) | 1.90, m | 2.00, m |
| 8 | 4.15, dd (13.1, 6.2) | 4.53, d (13.4) | 4.16, d (8.2) | 4.33, brs | 4.27, brs |
| 9 | 3.57, dd (13.1, 8.0) | 4.69, d (13.4) | 3.43, dd (8.2, 11.9) | 4.29, d (8.0) | 4.51, br m |
| 2' | 4.57, dd (10.4, 7.1) | 4.45, dd (10.3, 7.0) | |||
| 3'α | 2.02, m (overlap) | 2.56, m (overlap) | 2.48, m (overlap) | 2.21, m (overlap) | 2.33, m (overlap) |
| 3'β | 2.92, dd (13.1, 7.1) | 2.04, ddd (12.4, 10.3, 8.3) | 2.08, t (12.7) | 2.28, m (overlap) | 2.53, dd (12.9, 4.5) |
| 4' | 3.24, dd (12.8, 6.7) | 3.12, m (overlap) | 2.30, m | 3.40, m | 3.47, td (13.0, 4.5) |
| 5' | 4.08, d (8.8) | ||||
| 6' | α 2.36, m (overlap) β 2.56, ddd (17.5, 6.3, 1.8) | α 2.60, m (overlap) β 2.28, dt (16.4, 5.6) | 5.55, d (10.0) | α 2.59, ddd (18.2, 12.4, 5.2) β 2.27, m (overlap) | 6.01, d (10.0) |
| 7' | α 2.12, m β 2.04, m (overlap) | α 1.74, m β 1.95, dt (12.5, 5.6) | 5.69, d (10.0) | α 1.58, m β 2.27, m (overlap) | 6.86, d (10.0) |
| 8' | 3.66, m | 4.36, m (overlap) | 4.16, d (8.2) | 4.00, dd (13.2, 7.4) | 4.60, d (8.2) |
| 9' | 4.45, dd (12.8, 8.2) | 4.36, m (overlap) | 3.43, dd (8.2, 11.9) | 3.65,dd (13.2, 8.8) | 3.86, dd (13.0, 8.2) |
| 2-SMe | 2.09, s | 2.10, s | 2.15, s | 1.93, s | 2.09, s |
| 2'-SMe | 2.15, s | 2.07, s | 2.22, s | ||
| 5-OH | 5.31, brs | ||||
| 5'-OH | 5.31, brs | ||||
| 8-OH | 5.68, s | 5.87, s | 5.36, brs | 4.83, brs | |
| 8'-OH | 5.41, brs | 5.87, s | 5.89, s | 6.21, s |
a Measured in CDCl3, b Measured in DMSO-d6, c Measured in acetone-d6.