Table 1.
1H and 13C NMR chemical shifts for compounds 1–4.
| Position | 1 | 2 | 3 | 4 | ||||
|---|---|---|---|---|---|---|---|---|
| δH, m (J in Hz) a | δC b, type | δH, m (J in Hz) a | δC b, type | δH, m (J in Hz) c | δC d, type | δH, m (J in Hz) c | δC d, type | |
| 1 | 160.7, C | 160.6, C | 160.6, C | 159.8, C | ||||
| 2 | 5.44, dd (10.0, 1.6) |
77.8, CH | 5.43, dd (10.0, 1.6) |
77.8, CH | 4.91, dd (10.0, 1.6) |
78.4, CH | 4.98, d (10.4) |
77.8, CH |
| 3 | 4.90, d (10.0) |
122.2, CH | 4.91, d (10.0) |
122.7, CH | 4.55, d (10.0) |
123.9, CH | 4.45, d (10.4) |
123.5, CH |
| 4 | 141.6, C | 140.8, C | 140.2, C | 139.4, C | ||||
| 5α | 2.20, m | 47.9, CH2 | 2.18, dd (12.4, 10.8) |
42.6, CH2 | 2.42, dd (12.0, 3.2) |
49.1, CH2 | 1.98, m | 49.3, CH2 |
| 5β | 2.76, dd (12.8, 5.2) |
2.87, dd (12.4, 4.4) |
189, m | 2.25, dd (12.8, 3.6) |
||||
| 6 | 4.70, ddd (10.4, 10.4, 5.2) |
65.2, CH | 4.97, ddd (10.8, 9.2, 4.4) |
78.3, CH | 3.84, dd (9.2, 9.2) |
69.6, CH | 4.21, ddd (11.2, 9.2, 3.6) |
64.8, CH |
| 7 | 5.20, d (10.4) | 128.1, CH | 5.05, d (9.2) | 123.1, CH | 5.09, d (9.2) | 131.6, CH | 4.84, d (9.2) | 131.2, CH |
| 8 | 139.8, C | 144.2, C | 138.4, C | 139.4, C | ||||
| 9α | 2.03, m | 36.8, CH2 | 2.07, m | 36.9, CH2 | 2.21, ddd (13.6, 13.6, 2.4) |
28.2, CH2 | 1.58, m | 28.5, CH2 |
| 9β | 2.38, m | 2.42, m | 1.63, m | 2.30, dd (13.2, 4.8) |
||||
| 10α | 1.29, m | 23.5, CH2 | 1.35, m | 23.6, CH2 | 1.16, m | 23.9, CH2 | 1.60, m | 22.7, CH2 |
| 10β | 2.51, m | 2.17, m | 1.84, m | 1.28, m | ||||
| 11 | 2.42, dd (10.8, 2.8) |
61.4, CH | 2.43, m | 61.4, CH | 2.24, dd (10.4, 2.4) |
58.9, CH | 1.98, m | 62.6, CH |
| 12 | 60.8, C | 60.8, C | 59.7, CH | 60.9, C | ||||
| 13α | 2.03, m | 36.9, CH2 | 2.02, m | 37.0, CH2 | 1.49, m | 35.5, CH2 | 1.61, m | 37.1, CH2 |
| 13β | 1.06, m | 1.07, m | 0.98, m | 0.65, m | ||||
| 14α | 2.49, m | 23.7, CH2 | 2.52, m | 23.7, CH2 | 1.58, m | 22.2, CH2 | 2.08, m | 23.1, CH2 |
| 14β | 2.01, m | 2.03, m | 1.58, m | 1.65, m | ||||
| 15 | 123.8, C | 123.8, C | 123.8, C | 123.7, C | ||||
| 16 | 174.4, C | 174.4, C | 173.9, C | 174.3, C | ||||
| 17 | 1.86, s | 8.8, CH3 | 1.86, s | 8.7, CH3 | 1.64, s | 8.8, CH3 | 1.63, s | 8.8, CH3 |
| 18 | 1.70, s | 15.9, CH3 | 1.72, s | 15.9, CH3 | 1.31, s | 18.1, CH3 | 1.28, s | 16.9, CH3 |
| 19 | 1.86, s | 14.9, CH3 | 1.89, s | 15.3, CH3 | 1.45, s | 22.2, CH3 | 1.32, s | 21.8, CH3 |
| 20 | 1.33, s | 15.8, CH3 | 1.33, s | 15.8, CH3 | 1.00, s | 17.1, CH3 | 0.99, s | 16.4, CH3 |
| 6-OOH | 7.99, br s | |||||||
a Spectrum recorded at 400 MHz in CDCl3. b Spectrum recorded at 100 MHz in CDCl3. c Spectrum recorded at 400 MHz in C6D6. d Spectrum recorded at 100 MHz in C6D6.