Table 1.
The 1H and 13C{1H} NMR Spectroscopic Data of 1 and 2a,b Include the Results of 1H Iterative Functionalized Spin Analysis (HifSA) for the Precise Determination of the 1H NMR Spin Parameters.
| 1 |
2 |
||||
|---|---|---|---|---|---|
| Ring | no. | δH (J, Hz) | δ C | δH (J, Hz) | δ C |
| Unit I | |||||
| C | 2 | 101.71 s | 101.77 s | ||
| 3 | 3.977 dd (3.48, −0.30) | 66.27 d | 3.986 d (3.65) | 66.11 d | |
| 4 | 4.059 dd (3.48, 0.17) | 28.46 d | 4.077 dd (3.65, −0.48) | 28.18 d | |
| A | 5 | 154.20 s | 154.69 s | ||
| 6 | 6.259 dd (2.33, 0.17) | 97.64 d | 6.250 dd (2.33, −0.48) | 97.40 d | |
| 7 | 159.00 s | 158.98 s | |||
| 8 | 6.053 d (2.33) | 98.44 d | 6.038 d (2.33) | 98.68 d | |
| 9 | 156.86 s | 156.93 s | |||
| 10 | 101.97 s | 102.35 s | |||
| B | 1' | 130.33 s | 130.27 s | ||
| 2' | 7.074 d (2.24) | 115.91 d | 7.050 d (2.21) | 115.90 d | |
| 3' | 147.16 sc | 145.69 sc | |||
| 4' | 145.72 sc | 147.17 sc | |||
| 5' | 6.800 d (8.34) | 115.72 d | 6.779 d (8.34) | 115.64 d | |
| 6' | 6.960 dd (8.34, 2.24) | 120.14 d | 6.936 dd (8.34, 2.21) | 120.18 d | |
| Unit II | |||||
| F | 2 | 5.321 dddd (1.70, 1.01, −0.69, −0.37) | 79.15 d | 4.569 d (9.61) | 84.75 d |
| 3 | 4.081 dddd (1.94, 1.01, −0.40, −0.28) | 72.22 d | 4.176 dd (9.61, 8.97) | 73.61 d | |
| 4 | 4.253 dd (1.94, −0.20) | 38.36 d | 4.285 d (8.97) | 38.68 d | |
| D | 5 | 188.18 s | 186.85 s | ||
| 6 | 121.97 s | 122.33 s | |||
| 7 | 150.34 s | 150.11 s | |||
| 8 | 176.01 s | 175.53 s | |||
| 9 | 152.49 s | 152.35 s | |||
| 10 | 121.29 s | 123.30 s | |||
| E | 1' | 131.02 s | 130.29 s | ||
| 2' | 7.014 dd (2.07, −0.37) | 115.72 d | 6.982 d (2.10) | 116.35 d | |
| 3' | 146.05 s c | 146.77 s c | |||
| 4' | 145.95 s c | 146.11 s c | |||
| 5' | 6.758 dd (8.18, −0.28) | 115.60 d | 6.802 d (8.18) | 116.09 s c | |
| 6' | 6.831 ddd (8.18, 2.07, −0.69) | 119.80 d | 6.896 dd (8.18, 2.10) | 121.35 d | |
| Unit III | |||||
| I | 2 | 3.933 dd (1.05, −0.38) | 80.62 d | 3.585 ddd (1.33, −0.70, −0.51) | 79.73 d |
| 3 | 3.786 dddd (4.21, 2.71, 1.05, −0.19) | 67.06 d | 3.773 ddd (4.25, 2.26, 1.33) | 67.31 d | |
| 4a | 2.759 ddd (−15.93, 4.21, 0.13) | 30.76 t | 2.768 ddd (−16.60, 4.25, 0.42) | 29.88 t | |
| 4b | 2.750 dd (−15.93, 2.71) | 2.725 dd (−16.60, 2.26) | |||
| G | 5 | 156.58 s | 155.86 s | ||
| 6 | 6.098 ddd (−0.40, 0.20, 0.13) | 96.38 d | 6.067 d (0.42) | 96.76 d | |
| 7 | 155.36 s | 155.62 s | |||
| 8 | 107.22 s | 108.39 s | |||
| 9 | 155.62 s | 154.00 s | |||
| 10 | 100.00 s | 100.30 s | |||
| H | 1' | 131.04 s | 131.50 s | ||
| 2' | 6.538 dd (2.09, −0.38) | 114.75 d | 6.631 dd (2.09, −0.51) | 115.26 d | |
| 3' | 145.74 d c | 145.51 s c | |||
| 4' | 145.74 d c | 145.85 s c | |||
| 5' | 6.443 d (7.99) | 116.32 d | 6.557 d (8.09) | 116.04 d c | |
| 6' | 5.680 ddd (7.99, 2.09, −0.19) | 119.78 d | 6.192 ddd (8.09, 2.09, −0.70) | 119.68 d | |
a
1H and 13C NMR data were acquired in methanol-d4 at 600 and 150 MHz at 298 K, respectively.
b
The δH and J values were determined by HifSA.
c
Interchangeable assignment.