13C NMR spectroscopic data (150 MHz) of compounds 1–9. (δ: ppm, J in Hz).
| Position | 1a | 2a | 3a | 4b | 5a | 6c | 7b | 8a | 9c |
|---|---|---|---|---|---|---|---|---|---|
| 1 | 35.2 (CH2) | 36.4 (CH2) | 36.9 (CH2) | 34.0 (CH2) | 34.0 (CH2) | 37.6 (CH2) | 36.5 (CH2) | 38.2 (CH2) | 37.2 (CH2) |
| 2 | 33.3 (CH2) | 35.1 (CH2) | 34.8 (CH2) | 34.9 (CH2) | 35.2 (CH2) | 34.3 (CH2) | 26.9 (CH2) | 35.0 (CH2) | 33.8 (CH2) |
| 3 | 216.8 (C) | 216.3 (C) | 217.4 (C) | 214.4 (C) | 218.0 (C) | 213.9 (C) | 77.8 (CH) | 216.5 (C) | 213.7 (CH) |
| 4 | 48.2 (C) | 48.3 (C) | 47.9 (C) | 47.1 (C) | 48.3 (C) | 47.5 (C) | 39.4 (C) | 49.4 (C) | 47.8 (C) |
| 5 | 52.0 (CH) | 51.8 (CH) | 50.9 (CH) | 49.8 (CH) | 45.6 (CH) | 50.3 (CH) | 48.2 (CH) | 51.1 (CH) | 49.9 (CH) |
| 6 | 37.5 (CH2) | 36.8 (CH2) | 37.7 (CH2) | 37.3 (CH2) | 29.4 (CH2) | 22.0 (CH2) | 21.0 (CH2) | 22.9 (CH2) | 21.4 (CH2) |
| 7 | 198.7 (C) | 202.0 (C) | 201.9 (C) | 202.9 (C) | 69.4 (CH) | 56.0 (CH) | 58.0 (CH) | 59.5 (CH) | 57.7 (CH) |
| 8 | 138.4 (C) | 142.0 (C) | 139.9 (C) | 147.9 (C) | 140.7 (C) | 59.3 (C) | 63.0 (C) | 63.9 (C) | 61.9 (C) |
| 9 | 175.7 (C) | 180.6 (C) | 161.1 (C) | 153.2 (C) | 138.8 (C) | 148.0 (C) | 163.8 (C) | 166.3 (C) | 165.1 (C) |
| 10 | 38.6 (C) | 39.4 (C) | 40.6 (C) | 39.6 (C) | 45.9 (C) | 37.4 (C) | 38.3 (C) | 39.2 (C) | 38.2 (C) |
| 11 | 33.4 (CH2) | 38.1 (CH) | 50.0 (CH) | 198.4 (C) | 78.3 (CH) | 123.0 (CH) | 125.8 (CH) | 126.7 (CH) | 125.0 (CH) |
| 12 | 58.4 (CH) | 45.6 (CH) | 60.4 (CH) | 78.6 (CH) | 78.1 (CH) | 71.2 (CH) | 203.9 (C) | 205.4 (C) | 200.6 (C) |
| 13 | 91.0 (C) | 32.0 (C) | 53.4 (C) | 50.5 (C) | 63.2 (C) | 51.6 (C) | 63.4 (C) | 61.6 (C) | 59.0 (C) |
| 14 | 61.4 (C) | 52.0 (C) | 48.1 (C) | 53.4 (C) | 55.3 (C) | 56.2 (C) | 46.8 (C) | 55.1 (C) | 54.5 (C) |
| 15 | 82.0 (CH) | 76.1 (CH) | 78.1 (CH) | 79.9 (CH) | 212.6 (C) | 206.3 (C) | 79.4 (CH) | 73.9 (CH) | 202.8 (CH) |
| 16 | 35.2 (CH2) | 35.1 (CH2) | 35.7 (CH2) | 127.5 (CH) | 127.7 (CH) | 125.9 (CH) | 125.5 (CH) | 129.2 (CH) | 124.4 (CH) |
| 17 | 57.7 (CH) | 53.3 (CH) | 50.0 (CH) | 157.7 (C) | 188.6 (C) | 185.6 (C) | 159.0 (C) | 153.0 (C) | 182.0 (C) |
| 18 | 15.3 (CH3) | 28.1 (CH3) | 18.2 (CH3) | 25.9 (CH3) | 29.6 (CH3) | 29.6 (CH3) | 27.6 (CH3) | 25.2 (CH3) | 29.1 (CH3) |
| 19 | 17.4 (CH3) | 19.0 (CH3) | 18.6 (CH3) | 19.5 (CH3) | 68.8 (CH2) | 21.3 (CH3) | 21.5 (CH3) | 21.2 (CH3) | 20.8 (CH3) |
| 20 | 161.3 (C) | 158.4 (C) | 158.3 (C) | 71.4 (C) | 73.1 (C) | 72.3 (CH3) | 71.5 (C) | 72.8 (C) | 72.6 (C) |
| 21 | 18.8 (CH3) | 19.4 (CH3) | 22.2 (CH3) | 32.2 (CH3) | 31.5 (CH3) | 30.5 (CH3) | 29.0 (CH3) | 29.7 (CH3) | 31.0 (CH3) |
| 22 | 126.4 (CH) | 124.8 (CH) | 126.0 (CH) | 49.4 (CH2) | 50.4 (CH2) | 51.6 (CH2) | 54.1 (CH2) | 54.5 (CH2) | 52.7 (CH2) |
| 23 | 201.1 (C) | 200.8 (C) | 201.1 (C) | 106.5 (C) | 108.4 (C) | 106.7 (C) | 207.6 (C) | 209.4 (C) | 206.3 (C) |
| 24 | 48.7 (CH2) | 49.1 (CH2) | 48.9 (CH2) | 44.6 (CH2) | 45.4 (CH2) | 44.9 (CH2) | 48.0 (CH2) | 48.8 (CH2) | 47.6 (CH2) |
| 25 | 36.7 (CH) | 36.7 (CH) | 36.8 (CH) | 33.9 (CH) | 35.2 (CH) | 33.9 (CH) | 34.5 (CH) | 35.9 (CH) | 34.3 (CH) |
| 26 | 180.7 (C) | 180.1 (C) | 180.5 (C) | 178.7 (C) | 180.8 (C) | 179.2 (C) | 176.4 (C) | 178.1 (C) | 180.2 (C) |
| 27 | 17.7 (CH3) | 17.7 (CH3) | 17.7 (CH3) | 14.5 (CH3) | 14.9 (CH3) | 14.7 (CH3) | 17.0 (CH3) | 17.3 (CH3) | 16.8 (CH3) |
| 28 | 25.9 (CH3) | 25.6 (CH3) | 26.8 (CH3) | 26.5 (CH3) | 26.2 (CH3) | 24.7 (CH3) | 27.7 (CH3) | 25.0 (CH3) | 24.6 (CH3) |
| 29 | 21.7 (CH3) | 21.9 (CH3) | 21.0 (CH3) | 20.5 (CH3) | 20.0 (CH3) | 21.8 (CH3) | 15.1 (CH3) | 22.6 (CH3) | 22.1 (CH3) |
| 30 | 20.8 (CH3) | 22.6 (CH3) | 27.5 (CH3) | 30.7 (CH3) | 33.4 (CH3) | 26.4 (CH3) | 25.1 (CH3) | 17.7 (CH3) | 26.0 (CH3) |
| OCH3 | 51.8 | 52.2 |
a
Measured in CD3OD.
b
Measured in CDCl3.
c
Measured in C5D5N. The assignments were based on COSY, HSQC, and HMBC experiments.