Table 2.
NMR spectroscopic data for compound 2a and 2b.
| No. | 2a | No. | 2b | ||
|---|---|---|---|---|---|
| δ Ca,b | δ Ha,c (J in Hz) | δ Ca,b | δ Ha,c (J in Hz) | ||
| 1 | 84.1 (d) | 4.62 (1H, dd, 5.8, 9.4) | 1 | 83.8 (d) | 4.61 (1H, dd, 5.0, 10.0) |
| 2 | 25.4 (t) | 1.77 (2H, overlapped) | 2 | 25.7 (t) | 1.76 (2H, overlapped) |
| 3 | 38.3 (t) |
1.47 (1H, overlapped) 1.32 (1H, td, 5.6, 12.6) |
3 | 38.2 (t) |
1.46 (1H, overlapped) 1.35 (1H, td, 4.8, 12.8) |
| 4 | 33.0 (s) | − | 4 | 32.9 (s) | − |
| 5 | 52.8 (d) | 1.04 (1H, d, 10.6) | 5 | 52.7 (d) | 1.17 (1H, d, 11.5) |
| 6 | 27.5 (t) |
1.89 (1H, d, 12.6) 1.83 (1H, m) |
6 | 25.3 (t) |
2.01 (1H, m) 1.76 (1H, overlapped) |
| 7 | 73.2 (d) | 4.21 (1H, d, 12.5) | 7 | 76.4 (d) | 5.41 (1H, dd, 4.5, 11.8) |
| 8 | 61.5 (s) | − | 8 | 60.9 (s) | − |
| 9 | 55.9 (d) | 1.78 (1H, d, 8.2) | 9 | 55.2 (d) | 1.76 (1H, overlapped) |
| 10 | 45.8 (s) | − | 10 | 47.2 (s) | |
| 11 | 20.5 (t) |
1.70 (1H, dd, 4.7, 15.2) 1.44 (1H, overlapped) |
11 | 20.2 (t) | 1.46 (1H, overlapped) |
| 12 | 30.6 (t) |
2.71 (1H, 1H, tt, 5.5, 7.3) 1.61 (1H, m) |
12 | 30.4 (t) |
2.54 (1H, overlapped) 1.56 (1H, m) |
| 13 | 38.3 (d) | 3.10 (1H, br.s) | 13 | 38.2 (d) | 3.11 (1H, br.s) |
| 14 | 76.9 (d) | 6.02 (1H, br.s) | 14 | 75.0 (d) | 4.99 (1H, br.s) |
| 15 | 205.0 (s) | − | 15 | 205.8 (s) | − |
| 16 | 146.3 (s) | − | 16 | 147.1 (s) | − |
| 17 | 117.4 (t) | 6.11 (1H, s) 5.39 (1H, s) | 17 | 118.0 (t) | 6.12 (1H, s) 5.41(1H, s) |
| 18 | 33.3 (q) | 0.88 (3H, s) | 18 | 33.0 (q) | 0.92 (3H, s) |
| 19 | 21.9 (q) | 0.86 (3H, s) | 19 | 22.0 (q) | 0.85 (3H, s) |
| 20 | 61.1 (t) |
4.44 (1H, d, 13.6) 4.27 (1H, dd, 2.4, 13.6) |
20 | 61.6 (t) |
4.00 (1H, d, 13.6) 4.39 (1H, dd, 2.4, 13.6) |
| 1-OAc | 171.3 (s) | − | 1-OAc | 168.9 (s) | − |
| 1-OAc | 22.1 (q) | 2.03 (3H, s) | 1-OAc | 22.0 (q) | 2.02 (3H, s) |
| 14-OAc | 170.4 (s) | − | 7-OAc | 168.2 (s) | − |
| 14-OAc | 21.6 (q) | 1.96 (3H, s) | 7-OAc | 21.8 (q) | 1.99 (3H, s) |
aMeasured in CDCl3.
bMeasured at 125 MHz.
cMeasured at 500 MHz.