Table 2.
1H NMR spectroscopic data (δ) for compounds 1−4a (δ in ppm, J in Hz).
| No. | 1 | 2 | 3 | 4 |
|---|---|---|---|---|
| 1 | 1.94, overlap | 1.70, td (13.8, 3.5) | 3.57, d (3.0) | 1.66, overlap |
| 1.59, m | 1.14, d (12.5) | 1.26, br d (12.8) | ||
| 2 | 2.31, m | 1.98, overlap | 2.10, overlap | 1.98, overlap |
| 2.03, overlap | 1.56, d (11.6) | 1.64, overlap | 1.57, m | |
| 3 | 4.34, br d (5.5) | 4.22, br s | 1.72, td (13.7, 4.0) | 5.21, br s |
| 1.50, overlap | ||||
| 6 | 4.04, br s | 2.03, td (13.8, 2.4) | 3.92, br s | |
| 1.62, overlap | ||||
| 7 | 3.14, t (12.9) | 2.11, m | 1.87, overlap | 1.62, overlap |
| 2.09, dd (13.0, 4.9) | 1.35, overlap | 1.24, br d (12.1) | ||
| 8 | 1.94, overlap | 1.77, m | 1.52, overlap | 1.41, m |
| 9 | 2.71, m | 2.09, m | 2.56, m | 1.72, overlap |
| 11 | 2.22, m | 2.01, overlap | 2.12, overlap | 1.70, overlap |
| 2.02, overlap | 1.95, overlap | 1.84, overlap | 1.00, qd (13.0, 3.6) | |
| 12 | 5.66, br s | 5.63, t (3.5) | 5.63, t (3.8) | 2.35, d (12.9) |
| 1.98, overlap | ||||
| 14 | 2.47, m | 2.32, m | 2.38, m | 2.25, t (9.8) |
| 15 | 1.08, d (7.0) | 0.87, d (6.8) | 0.92, d (6.9) | 5.62, ddd (17.2, 9.8, 9.8) |
| 16 | 6.25, dd (17.7, 10.9) | 6.20, dd (17.6, 10.9) | 6.20, dd (17.6, 10.9) | 5.13, dd (10.2, 2.0) |
| 4.98, dd (17.2, 2.0) | ||||
| 17 | 5.09,d (17.7) | 5.08,d (17.6) | 5.07,d (17.6) | 4.64, d (1.1) |
| 4.92, d (10.9) | 4.90, d (10.9) | 4.89, d (10.9) | 4.48, br s | |
| 18 | 1.50, s | 1.36, s | 1.12, s | 1.32, s |
| 20 | 0.89, s | 0.96, s | 0.70, s | 0.91, s |
| 1-OH | 5.50, d (4.0) | |||
| 3-OH | 6.23, br s | 6.23, d (2.5) | ||
| 5-OH | 6.10, br s | 5.15, s | 6.20, br s | |
| 6-OH | 7.21, br s | |||
| 19-OH | 12.11, s | 14.32, br s |
NMR data (δ) were measured at 500 MHz in CD3OD for 1 and at 600 MHz in DMSO-d6 for 2−4.