Table 1.
1H NMR data of 1–6 in CDCl3 (δH in ppm, J in Hz within the parenthesis).
| No. | 1a | 2a | 3b | 4b | 5b | 6a |
|---|---|---|---|---|---|---|
| 1 | 6.65, d (12.3) | 6.66, d (12.3) | 6.68, d (12.3) | 6.58, d (12.2) | 6.05, d (12.7) | 6.00, d (12.8) |
| 2 | 5.82, d (12.0) | 5.81, d (12.0) | 5.83, d (12.1) | 6.21, d (12.0) | 5.94, d (12.6) | 5.93, d (12.7) |
| 3 | – | – | – | – | – | – |
| 4 | – | – | – | – | – | – |
| 5 | 2.44, m | 2.48, m | 2.47, m | – | 2.42, dd (13.0, 4.7); 1.62, m | 2.54, d (3.5) |
| 6 | 2.27, m | 2.25, m | 3.12, 2.59 m | 3.20, t (13.4, 1); 2.34, m |
1.90, m; 0.76, m | 5.31, brs |
| 7 | 1.92, m | 1.91, m | 2.13, 1.94 m | 2.04, m; 2.40, m | 1.18, m | 1.84, m |
| 8 | – | – | – | – | 1.62, m | 1.78, dd (13.5, 4.0) |
| 9 | – | – | – | – | – | – |
| 10 | – | – | – | – | – | – |
| 11 | 2.10, m | 2.10, m | 2.81, m; 2.13, m | 2.80, dd (19.6, 8.0); 2.49 d (19.6) |
2.00, dd (15.2, 5.2); 2.32, m | 2.01, m |
| 12 | 5.14, d (7.4) | 5.31, d (7.2) | 5.03, d (7.5) | 4.94, d (7.9) | 4.85, dd (8.8, 5.3) | 4.87, dd (9.2, 5.7) |
| 13 | – | – | – | – | – | – |
| 14 | – | – | – | – | – | – |
| 15 | 1.45, m | 1.44, m | 1.74, 1.44 m | 1.67, m; 131, m | 1.39, m | 1.30, m |
| 16 | 1.25, m | 1.71, m | 2.15, 1.53, m | 1.89, m; 1.51, m | 1.46, m | 1.25, m |
| 17 | 3.55, dd (10.9, 7.5) | 2.70, m | 2.66, m | 2.11, m | 2.22, m | 2.23, m |
| 18 | 0.71, s | 0.96, s | 0.75, s | 0.76, s | 1.01, s | 1.05, s |
| 19 | 6.14, s | 6.16, s | 6.18, s | 4.61, s | 1.15, d (2.6), 1.38 (overlapped) |
1.30, dd (4.7) |
| 20 | – | – | 2.04, m | 2.10, m | 2.01, m | 2.02, m |
| 21 | 2.75, dd (3.3) | 1.33, s | 0.98, d (7.0) | 0.89, d (6.5) | 0.85, d (6.7) | 0.86, d (6.7) |
| 22 | 4.49, dd (12.7, 3.7) | 4.14, dd (12.7, 3.8) | 4.34, dd (9.4, 2.5) | 4.46, d (13.1) | 4.48, dt (13.0, 3.2) | 4.48, dd (9.8, 3.3) |
| 23 | 2.03, m | 2.32, m | 4.56, br. d (7.7) | 2.36, m; 2.11, m | 2.11, m | 2.14, m |
| 24 | 6.51, dd (4.8, 1.6) | 6.60, dd (4.6, 1.7) | 6.480, s | 6.60, s | 6.61, d (6.0) | 6.61, d (6.0) |
| 25 | – | – | – | – | – | – |
| 26 | – | – | – | – | – | – |
| 27 | 1.90, s | 1.91, s | 1.93, s | – | 1.92, s | 1.92, s |
| 28 | 1.53, s | 1.54, s | 126, s | 1.13, s | 1.35, s | 1.47, s |
| 29 | 1.41, s | 1.41, s | 1.54, s | 1.64, s | 1.38, s | 1.42, s |
| 30 | 1.39, s | 1.32, s | 1.41, s | 1.67, s | 1.01, s | 1.03, s |
| OCOCH3-12 | 2.12, s | 2.13, s | 2.09, s | 2.05, s | 2.04, s | 2.04, s |
| OCOCH3-6 | – | – | – | – | – | 2.05, s |
a
Recorded at 500 MHz.
b
Recorded at 600 MHz.
Internal standard: TMS; In 1H-NMR s, brs, d, dd, and m represent singlet, broad singlet, doublet, double doublet, and multiplet or overlapped signals, respectively.