Table 2.
1H NMR spectral data for compounds 1 to 4.
| Position | 1 a | 2 b | 3 b | 4 c |
|---|---|---|---|---|
| 2 | 4.96 d (9.5) d | 5.05 d (10.8) | 5.25 m | 5.59 d (16.0) |
| 3 | 2.89 dd (10.0, 10.0) | 2.37 dd (7.8, 9.6) | 3.56 d (9.6) | 6.05 d (16.0) |
| 5 | 1.52 2H, m | 1.72 m; 1.65 m | 1.48 m; 2.11 m | 1.52 m; 1.99 m |
| 6 | 1.94 m; 1.64 m | 1.88 m; 1.76 m | 2.13 m; 2.23 m | 2.22 m; 2.35 m |
| 7 | 2.63 m | 2.65 ddd (6.6, 7.8, 9.6) | 5.22 m | 5.34 dd (7.5, 7.5) |
| 9 | 1.85 ddd (13.0, 13.0, 3.0); 1.20 ddd (13.0, 13.0, 4.5) | 1.88 m; 2.00 m | 2.14 m; 2.24 m | 1.96 m; 2.18 m |
| 10 | 1.94 m; 1.68 ddd (13.0, 10.5, 3.0) | 2.14 m | 1.09 m; 1.61 m | 2.04 m; 2.23 m |
| 11 | 4.27 dd (11.0, 4.5) | 4.99 dd (7.6, 7.6) | 3.12 dd (5.6, 5.6) | 5.18 dd (9.0, 3.5) |
| 13 | 2.66 m; 2.20 dd (11.5, 5) | 2.03 m; 1.92 m | 5.49 d (7.6) | 2.10 m; 2.15 d (3.0) |
| 14 | 2.79 ddd (11.5, 11.5, 4.5); 2.00 m | 2.40 dd (14.4, 7.2); 1.94 ddd (14.4, 12.0, 3.0) |
5.89 d (7.6) | 1.86 td (12.5, 3.5); 1.60 m |
| 15 | 2.22 sept (7.0) | |||
| 16 | 0.97 3 H, d (7.0) | 1.06 3H, d (7.2) | 1.02 3H, d (6.4) | 0.87 3H, d (7.0) |
| 17 | 0.90 3 H, d (7.0) | 1.02 3H, d (6.8) | 1.02 3H, d (6.4) | 0.87 3H, d (7.0) |
| 18 | 0.99 3 H, s | 1.14 3H, s | 1.33 3H, s | 1.40 3H, s |
| 19 | 1.05 3 H, s | 1.25 3H, s | 1.64 3H, s | 1.60 3H, s |
| 20 | 4.93 s; 4.97 s | 1.67 3H, s | 1.26 3H, s | 1.67 3H, s |
| 13-OAc | 2.14 3H, s | |||
| 14-OAc | 2.01 3H, s | |||
| 1-OH | 2.39 s | |||
| 11-OOH | 7.64 br s |
a Spectrum recorded in C6D6 at 500 MHz at 25 °C, b Spectra recorded in CDCl3 at 400 MHz at 25 °C, c Spectrum recorded in CDCl3 at 500 MHz at 25 °C, d J values (Hz) in parentheses.