Table 1. NMR Data for Trichothilone A (1)a in DMSO-d6 (500 MHz for 1H NMR, 125 MHz for 13C NMR).
position | δC, type | δH (J in Hz) | HMBC | COSY |
---|---|---|---|---|
1 | 175.5, C | |||
2 | 35.5, CH | 2.44, ovlpb | 1, 3, 22 | 22, 3a, 3b |
3a | 40.0, CH2 | 1.32, m | 2, 4, 22, 23 | 2, 4 |
3b | 1.16, m | 2, 4, 22, 23 | 2, 4 | |
4 | 29.1, CH | 1.42, ovlp | 3, 5, 6, 23 | 3b, 5, 23 |
5 | 34.9, CH2 | 1.06, ovlp | 6, 23 | 4, 6a, 6b |
6a | 25.0, CH2 | 1.70, m | 5, 7a, 7b | |
6b | 1.59, m | 5, 7a | ||
7a | 29.9, CH2 | 2.73, m | 6, 8 | 6b |
7b | 2.49, m | 6a | ||
8 | 156.0, C | |||
9 | 112.8, CH | 7.01, s | 8, 10 | |
10 | 169.1, C | |||
11a | 31.2, CH2 | 2.96, ddd (14.9, 6.7, 3.8) | 10, 13 | 12 |
11b | 2.77, m | 10, 13 | 12 | |
12 | 26.0, CH2 | 1.75, m | 11a, 11b, 13a, 13b | |
13a | 32.5, CH2 | 1.40, ovlp | 12, 14 | |
13b | 1.13, ovlp | 12, 14 | ||
14 | 68.9, CH | 3.18, m | 13a, 13b, 15, OH | |
OH | 4.19, br | 14 | ||
15 | 38.8, CH | 1.51, p (7.0) | 16, 24 | 16, 24 |
16 | 76.7, CH | 4.81, ddd (9.5, 7.2, 2.5) | 1, 25 | 15, 17 |
17 | 30.5, CH | 1.80, m | ||
16, 18, 25 | ||||
18 | 41.0, CH2 | 1.01, m | 17, 19, 25, 26 | 17, 19 |
19 | 26.9, CH | 1.42, ovlp | 18, 26 | |
20a | 34.2, CH2 | 1.38, ovlp | 19, 26 | 19, 21 |
20b | 1.19, ovlp | 19, 21, 26 | 19, 21 | |
21 | 44.5, CH2 | 3.25, t (7.4) | 19, 20, 28 | 20a, 20b |
22 | 16.4, CH3 | 1.01, d (6.8) | 1, 2, 3 | 2 |
23 | 19.9, CH3 | 0.81, d (6.8) | 3, 4, 5 | 4 |
24 | 9.4, CH3 | 0.71, ovlp | 14, 15 | 15 |
25 | 12.3, CH3 | 0.73, ovlp | 16, 17, 18 | 17 |
26 | 19.3, CH3 | 0.80, d (6.8) | 18, 19, 20 | 19 |
27 | 34.3, CH3 | 2.88, s | 21, 28 | |
28 | 172.1, C | |||
29 | 25.8, CH2 | 2.24, m | 28, 30 | 30 |
30 | 9.2, CH3 | 0.94, t (7.4) | 28, 29 | 29 |
Z-conformer chemical shift values.
Overlapping signals.