Table 2. 1H NMR Data for Compounds 2–9 in CDCl3 at 600 MHz.
|
2 |
3 |
4 |
5 |
6 |
7 |
8a |
9 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δH | δH′ | δH/δH′ | δH | δH′ | δH | δH′ | δH | δH′ | δH | δH′ | δH | δH′ | δH/δH′ | |
| 2,2′ | 5.79 m | 5.67 m | 5.79 d (15.59) | 5.69 m | 5.82 m | 5.79 d (15.48) | 5.68 d (12.47) | 5.81 d (15.68) | 5.80 m | 5.66 d (12.72) | 5.80 d (15.6) | 5.80 d (15.62) | ||
| 3,3′ | 6.51 (d (12.6) | 7.50 d (15.6) | 7.53 (d 15.56) | 6.46 d (12.41) | 7.39 d (15.56) | 7.57 d (15.55) | 7.52 d (15.56) | 6.52 d (12.62) | 7.44 d (15.54) | 7.47 d (15.63) | 6.46 d (12.69) | 7.55 d (15.6) | 7.47 d (15.62) | |
| 4,4′-Me | 1.86 s | 1.77 s | 1.82 s | 1.84 s | 1.82 s | 1.75 s | 1.82 s | 1.86 s | 1.81 s | 1.78 s | 1.86 s | 1.83 s | 1.80 s | |
| 5,5′ | 5.84 dd (7.06, 6.27) | 6.1 dd, (6.53, 6.40) | 6.31 dd (7.55, 7.37) | 5.98 t (6.33) | 6.09 t (6.23) | 6.33 m | 6.32 m | 5.86 t (7.00) | 6.14 t (6.87) | 6.11 t (6.88) | 5.97 br s | 6.35 m | 6.19 t (7.03) | |
| 6,6′ | 2.55 dd (14.73, 5.62) | 2.62 br d (13.34) | 2.59 ddd (2.85, 6.14, 14.47) | 2.56 m | 2.64 m | 2.50 d (13.39) | 2.67 d (12.99) | 2.57 ddd (4.06, 6.48, 13.87) | 2.69 ddd (4.38, 6.03, 11.73) | 2.59 m | 2.57 m | 2.60 m | 2.47 ddd (3.24, 7.14, 14.94) | |
| 2.38 m | 2.28 m | 2.37 dt (8.86, 14.34) | 2.34 m | 2.36 m | 2.35 m | 2.35 m | 2.40 dt (7.02, 15.36) | 2.28 dt (7.45, 15.12) | 2.34 m | 2.41 dt (7.38, 14.56) | 2.38 m | 2.31 dt (7.56, 15.19) | ||
| 7,7′ | 4.06 m | 4.04 m | 4.01 m | 4.02 m | 3.99 m | 3.97 m | 4.00 m | 4.03 m | 3.97 m | 4.08 m | 4.04 ddd (4.25, 7.90, 11.76) | |||
| 8,8′ | 2.28 m | 2.25 ddd (5.02, 9.81, 15.0) | 2.10 m | 2.29 m | 2.10 m | 2.10 m | 2.19 m | 2.05 m | 2.26 m | 1.89 m | ||||
| 1.54 m | 1.63 m | 1.64 m | 1.67 m | 1.55 m | 1.67 m | 1.54 m | 1.64 m | 1.62 m | 1.52 m | |||||
| 9,9′ | 4.30 m | 4.30 m | 4.36 m | 4.21 d (11.37) | 4.31 brs | 4.29 m | 4.39 m | 4.28 m | 4.38 m | 4.29 m | 4.34 d (10.74) | |||
| 10,10′ | 5.70 m | 5.74 m | 5.74 m | 5.72 m | 5.78 m | 5.69 m | 5.78 m | 5.71 m | 5.74 m | 5.65 m | ||||
| 11,11′ | 5.80 m | 5.74 m | 5.80 m | 5.80 m | 5.71 m | 5.80 m | 5.69 m | 5.74 m | 5.77 m | 5.81 m | ||||
| 12,12′ | 2.01 m | 1.97 m | 1.96 m | 2.08 d (17.61) | 1.97 m | 1.95 m | 1.97 m | 1.98 m | ||||||
| 1.98 m | ||||||||||||||
| 13,13′ | 3.67 m | 3.63 m | 3.64 m | 3.69 m | 3.68 m | 3.79 m | 3.64 m | 3.68 m | ||||||
| 14,14′ | 1.87 m | 1.78 m | 1.87 m | 1.84 m | 1.88 m | 1.84 m | 1.77 m | 1.86 m | ||||||
| 1.62 m | 1.64 m | 1.55 m | 1.63 m | 1.56 m | 1.58 m | 1.64 m | 1.59 m | |||||||
| 15,15′ | 4.06 m | 4.01 m | 3.78 m | 4.05 m | 3.78 ma | 3.82 ma | 3.82 m | 4.08 m | 3.83 m | |||||
| 16,16′ | 1.54 m | 1.51 m | 1.55 m | 1.59 m | 1.65 m | 1.63 m | 1.66 m | 1.68 m | ||||||
| 16,16′-Me | 0.81 d (6.0) | 0.82 d (6.0) | 0.78 d (6.98) | 0.83 d (6.54) | 0.84 d (6.32) | 0.80 d (7.14) | 0.78 d (7.02) | 0.82 d (6.91) | 0.81 d (7.13) | 0.83 d (7.13) | 0.84 d (7.75) | 0.79 d (6.36) | 0.78 d (6.35) | 0.83 d (7.02) |
| 17,17′ | 3.85 m | 3.84 t (9.70) | 3.80 m | 3.88 m | 3.76 m | 3.86 m | 3.85 m | 3.84 m | ||||||
| 18,18′ | 1.76 m | 1.70 m | 1.79 m | 1.74 m | 1.70 m | 1.85 m | 1.72 m | 1.87 m | ||||||
| 1.63 m | 1.41 m | 1.41 m | 1.55 m | 1.55 m | 1.50 m | 1.41 m | 1.50 m | |||||||
| 19,19′ | 3.93 m | 3.88, m | 3.88 t, (10.55) | 3.85 m | 3.79 m | 3.99 m | 3.88 m | 3.88 m | 3.87 m | 3.85 m | 3.90 m | 3.84 m | ||
| 20,20′ | 1.94 m | 1.87 t (12.35) | 1.87 m | 1.90 m | 1.87 m | 1.87 m | 1.85 m | 1.89 m | ||||||
| 1.53 m | 1.52 m | 1.53 m | 1.55 m | 1.53 m | 1.57 m | 1.53 m | 1.55 m | |||||||
| 21,21′ | 5.63 d (9.82) | 5.71 m | 5.56 d (11.09) | 5.64 m | 5.66 m | 5.71 m | 5.60 d (10.39) | 5.63 d (10.00) | 5.65 m | 5.69 m | 5.55 d (11.17) | 5.65 m | ||
| 22,22′ | 1.64 m | 1.65 m | 1.64 m | 1.69 m | 1.76 m | 1.73 m | 1.76 m | 1.74 m | ||||||
| 22,22′-Me | 0.87 d (6.81) | 0.89 d (6.86) | 0.90 d (6.89) | 0.87 d (8.45) | 0.89 d (7.47) | 0.91 d (6.92) | 0.89 d (7.13) | 0.89 d (6.78) | 0.88 d (6.78) | 0.86 d (7.03) | 0.90 d (6.95) | 0.91 m | 0.91 d (6.93) | |
| 23,23′ | 3.17 d (9.69) | 3.12 d (9.59) | 3.19 m | 3.09 m | 3.20 m | 3.15 d (9.39) | 3.12 d (9.83) | 3.12 m | 3.20 m | 3.14 dd (1.52, 9.66) | ||||
| 24,24′ | 1.67 m | 1.68 m | 1.69 m | 1.69 m | 1.68 m | 1.66 m | 1.68 m | 1.66 m | ||||||
| 24,24′-Me | 0.97 d (7.15) | 0.95 d (7.07) | 0.93 d (6.73) | 0.97 d (6.10) | 0.96 d (7.17) | 0.95 d (7.23) | 0.98 d(6.80) | 0.96 d (6.74) | 0.97 d (6.18) | 0.96 d (6.3) | 0.93 m | 0.98 d (6.74) | ||
| 25,25″ | 1.25 m | 1.34 m | 1.37 m | 1.35 m | 1.39 m | 1.35 m | 1.36 m | 1.37 m | ||||||
| 1.17 m | 1.25 m | 1.20 m | 1.24 m | 1.24 m | 1.21 m | 1.23 m | ||||||||
| 26,26′ | 1.88 m | 1.83 m | 1.86 m | 1.86 m | 1.87 m | 1.86 m | 1.84 m | 1.87 m | ||||||
| 1.25 m | 1.26 m | 1.25 m | 1.27 m | 1.25 m | 1.22 m | 1.26 m | 1.24 m | |||||||
| 27,27′ | 3.99 m | 3.98 m | 3.98 m | 3.98 m | 3.99 m | 3.97 m | 3.97 m | 3.98 m | ||||||
| 28,28′ | 1.82 m | 1.79 m | 1.82 m | 1.81 m | 1.82 m | 1.80 m | 1.79 m | 1.81 m | ||||||
| 1.59 m | 1.59 | 1.56 m | 1.59 m | 1.58 m | 1.57 m | 1.58 m | 1.58 m | |||||||
| 29,29′ | 3.53 m | 3.52 ddd 4.4, (9.83, 14.17) | 3.52 m | 3.52 m | 3.52 m | 3.52 m | 3.52 m | 3.52 m | ||||||
| 30,30′ | 1.99 m | 1.95 m | 1.97 m | 1.98 m | 1.99 m | 1.94 m | 1.97 m | 1.98 m | ||||||
| 1.18 m | 1.18 m | 1.16 m | 1.19 m | 1.18 m | 1.17 m | 1.17 m | 1.16 m | |||||||
| 31,31′ | 3.67 m | 3.69 dddd (2.88, 6.13, 12.0, 15.0) | 3.68 m | 3.69 m | 3.69 m | 3.67 m | 3.70 m | 3.69 m | ||||||
| 31,31′-Me | 1.18 d (6.36) | 1.17 d (6.14) | 1.20 d (6.18) | 1.20 d (5.9) | 1.17 d (5.90) | 1.19 d (6.44) | 1.19d (6.25) | 1.18 d (6.24) | 1.20 d (6.3) | 1.21 d (6.6) | 1.20 d (6.18) | |||
| 32,32′ | 4.67 d (6.91) | 4.74 d (6.80) | 4.43 d (6.64) | 4.39 m | 4.46 d (6.6) | 4.81 d (4.98) | 4.46 d (5.45) | 4.65 d (6.77) | 4.39 d (6.72) | 4.71 m | 4.43 d (6.29) | 4.47 d (6.69) | 4.53 d (5.45) | |
| 33,33′ | 4.82 (dd, 8.33, 7.02) | 3.28 t 7.15 | 3.29 m | 4.74 t 6.11 | 3.27 m | 4.83 dd (6.85, 8.39) | 3.52 m | 4.83 dd (7.18, 8.13) | 3.37 m | 3.40 m | 3.36 m | |||
| 34,34′ | 3.34 m | 3.24 m | 3.20 m | 3.32 m | 3.25 m | 3.35 m | 3.21 m | 3.31 m | 3.21 m | 3.21 m | 3.26 m | |||
| 35,35′ | 3.34 m | 3.24 m | 3.25 m | 3.31 m | 3.30 m | 3.31 m | 3.26 m | 3.61 m | 3.36 m | |||||
| 36,36′ | 4.05 m | 3.98 m | 3.99 m | 4.01 m | 3.99 m | 3.99 m | 3.99 m | 3.96 m | ||||||
| 3.28 m | 3.16 m | 3.21 m | 3.25 m | 3.25 m | 3.23 m | 3.18 m | 3.31 m | |||||||
| 38,38′ | 4.28 m | 4.20 brs | 4.13 m | 4.27 m | 4.21 m | |||||||||
| 39,39′ | 3.88 m | 3.70 m | 3.80 m | 3.81 m | ||||||||||
| 3.66 m | ||||||||||||||
| 15,15′-OMe | 3.34 s | 3.35 s | 3.35 s | 3.35 s | 3.33 s | 3.34 s | 3.32 s | 3.34 s | 3.32 s | 3.35 s | 3.36 s | 3.35 s | ||
| 29,29′-OMe | 3.32 s | 3.32 s | 3.34 s | 3.32 s | 3.32 s | 3.34 s | 3.34 s | 3.34 s | ||||||
| 34,34′-OMe | 3.48 s | 3.56 s | 3.59 s | 3.47 s | 3.56 s | 3.48 s | 3.58 s | 3.48 s | 3.58 s | 3.55 s | ||||
| 35,35′-OMe | 3.44 s | 3.45 s | 3.45 s | 3.44 s | 3.43 s | 3.45 s | 3.44 s | 3.44 s | 3.45s | 3.45 | ||||
a
The data at the same atom position could be exchanged.