Table 1. 1H NMR (500 MHz) Data for Compounds 1–11a.
| δH (J, Hz) |
||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| position | 1a+d | 1b+c | 2a | 2b | 3 | 4a+b | 5 | 6a | 6b | 7a+b | 8 | 9 | 10 | 11 |
| 3 | 6.24, d (10.2) | 6.23, d (10.2) | 6.45, d (9.9) | 6.52, d (10.2) | 6.30, d (10.6) | 6.74, d (8.4) | 6.40, d (9.9) | 6.23, d (10.1) | 6.21, d (10.1) | 6.72, d (8.4) | 6.32, d (10.4) | 6.73, d (8.3) | 6.21, d (10.6) | 6.72, d (8.4) |
| 4 | 7.23, d (10.2)/7.25, d (10.2)b | 7.23, d (10.2)/7.25, d (10.2)b | 6.61, d (9.9) | 6.89, d (10.2) | 9.06, d (10.6) | 7.34, d (8.4) | 6.66, d (9.9) | 7.21, d (10.1) | 7.21, d (10.1) | 7.3, d (8.4) | 8.18, d (10.4) | 7.45, d (8.3) | 8.71, d (10.6) | 7.30, d (8.4) |
| 5 | 6.47, s/6.49, sb | 6.47, s/6.49, sb | 6.84, s | 6.45, s | – | 6.58, s | 6.82, s | 6.43, s | 6.45, s | 6.54, s | 7.49, s | 6.42, s | – | 6.55, s |
| 9 | 1.68, m/1.67, m, 2.63, mb | 1.68, m/1.67, m, 2.63, mb | 1.92, m, 2.45, m | 1.43, m, 2.59, m | 8.19, d (8.8) | 1.76, ddd (14.4, 11.3, 6.5), 2.69, dd (14.4, 5.7) | 1.93, ddd (13.8, 10.0, 4.3), 2.47, m | 1.62, m, 2.62, dd (14.0, 5.5) | 1.66, m, 2.63, dd (13.9, 5.9) | 1.74, ddd (13.9, 11.7, 6.5), 2.68, dd (14.0, 6.0) | 8.15, d (8.8) | 2.71, mb | 7.62, d (8.3) | 1.74, ddd (14.1, 11.6, 6.4), 2.68, dd (14.1, 5.8) |
| 10 | 2.57, dd (20.2, 5.9), 2.83, m | 2.50, dd (20.3, 6.0), 2.85, m | 2.35, m, 2.83, m | 2.67, m, 2.89, m | 7.60, d (8.8) | 2.75, dd (17.3, 6.5), 3.06, m | 2.39, m, 2.87, ddd (13.8, 9.0, 4.3) | 2.53, dd (14.4, 5.9), 2.88, ddd (16.5, 10.6, 5.5) | 2.51, dd (20.4, 6.0), 2.86, ddd (20.2, 10.7, 6.0) | 3.09, m, 2.74, dd (17.3, 6.2) | 7.61, d (8.8) | 2.84, mb | 7.66, d (8.3) | 2.73, dd (17.3, 6.4), 3.09, m |
| 11 | 1.46, s | 1.42, s | 1.97, s | 1.91, s | 1.58, s | 2.16, s | 1.96, s | 1.46, s | 1.43, s | 2.17, s | 1.56, s | 2.22, s | 1.52, s | 2.16, s |
| 12 | 2.08, s | 2.08, s | 2.02, s | 2.00, s | 2.42, s | 2.09, s | 2.01, s | 2.07, s | 2.07, s | 2.09, s | 2.42, s | 1.49, s | 2.04, s | 2.08, s |
| 13 | 6.58, dd (17.8, 12.1) | 6.58, dd (17.8, 12.1) | 6.50, dd (17.9, 12.0) | 6.51, dd (17.9, 11.9) | 6.98, dd (17.9, 11.4) | 6.63, dd (17.9, 11.9) | 6.50, dd (17.8, 11.9) | 6.61, dd (17.9, 11.9) | 6.61, dd (17.9, 12.0) | 6.65, dd (17.9, 11.9) | 7.02, dd (17.7, 11.4) | 6.67, dd (17.8, 11.8) | 6.62, dd (17.9, 11.8) | 6.64, dd (17.9, 11.9) |
| 14 | 5.69, dd (12.1, 1.5), 5.83, dd (17.8, 1.5) | 5.69, dd (12.1, 1.5), 5.83, dd (17.8, 1.5) | 5.63, dd (12.0, 1.4), 5.78, dd (17.9, 1.4) | 5.67, dd (11.9, 1.5), 5.70, dd (17.9, 1.4) | 5.38, dd (17.9, 1.7), 5.82, dd (11.4, 1.7) | 5,66, dd (11.9, 1.7), 5.85, dd (17.9, 1.7) | 5.62, dd (11.9, 1.3), 5.80, dd (17.8, 1.3) | 5.68, dd (11.9, 1.3), 5.87, dd (17.9, 1.3) | 5.68, dd (12.0, 1.5), 5.89, dd (17.9, 1.5) | 5.65, dd (11.9, 1.5), 5.89, dd (17.9, 1.5) | 5.41, dd (17.7. 1.6), 5.84, dd (11.4, 1.6) | 5.55, dd (11.8, 1.3), 5.87, dd (17.8, 1.3) | 5.45, dd (17.9, 1.0), 5.82, d (11.8) | 5.65, dd (11.9, 1.7), 5.89, dd (17.9, 1.7) |
Measured in CDCl3.
Interchangeable. 1a+d: CH3O-1: 3.07, s; CH3O-8a: 2.92, s/2.93, s (interchangeable with 1b); 1b+c: CH3O-1: 3.12, s; CH3O-8a: 2.92, s/2.93,s (interchangeable with 1a); 2a: CH3O-4a: 3.04, s; CH3O-8a: 2.72, s; 2b: CH3O-4a: 3.10, s; CH3O-8a: 3.14, s; 3: CH3O-1: 3.08, s; CH3O-5: 3.79, s; 4a+b: CH3O-8a: 2.85, s; 5: C2H5O-4a (interchangeable with 8a): 2.76 dq (7.0, 14.1), 2.96, dq (7.0, 14.1) (CH2), 0.80, t (7.0) (CH3); C2H5O-8a (interchangeable with 4a): 3.08 dq (7.0, 14.1), 3.29, dq (7.0, 14.1) (CH2), 1.11, t (7.0) (CH3); 6a: C2H5O-1 (interchangeable with 8a): 2.93, m, 3.36 dq (14.3, 7.1) (CH2), 1.21, t (7.0) (CH3); C2H5O-8a (interchangeable with 1): 2.91, m, 3.19 dq (14.3, 7.1) (CH2), 1.01, t (7.0) (CH3); 6b: C2H5O-1:3.10, dq (14.2, 7.0), 3.34, dq (14.3, 7.1) (CH2), 1.23, t (7.0) (CH3); C2H5O-8a: 2.93, dq (14.2, 7.0), 3.17, dq (14.3, 7.1) (CH2), 0.97, t (7.0) (CH3); 7a+b: C2H5O-8a: 2.92, m, 3.11, m (CH2), 0.86, t (7.0) (CH3); 8: C2H5O-1: 3.00 dq (14.2, 7.0), 3.28 dq (14.2, 7.0) (CH2), 1.20, t (7.0) (CH3); 9: C2H5O-7: 3.13, dq (13.9, 7.1), 3.26, dq (14.0, 7.1) (CH2), 1.17, t (7.0) (CH3); 10: CH3-(CH2)3-O-1: 3.22, m, 2.92, m (1′-CH2), 1.58, m (2′-CH2), 1.28–1.40, m (3′-CH2), 0.87, t (7.4) (4′-CH3); CH3-(CH2)3-O-5: 3.14 m, 3.54, m (1″-CH2), 1.47, m (2″-CH2), 1.28–1.40, m (3″-CH2), 0. 81, t (7.5)/0.83, t (7.5) (4″-CH3) (interchangeable with 4‴-CH3); 3.10, m, 3.45, m (1‴-CH2), 1.47, m (2‴-CH2), 1.28–1.40, m (3‴-CH2), 0. 81, t (7.5)/0.83, t (7.5) (4‴-CH3) (interchangeable with 4″-CH3); 11: CH3-(CH2)3-O-8a: 2.83, m, 3.07, m (1′-CH2), 1.13–1.23, m (2′-CH2), 0.86–1.03, m (3′-CH2), 0.62, t (7.4) (4′-CH3).