Table 1.
NMR data for trichophycin B (17) and smenolactones B-D (2-4) (CD3OD, 700 MHz)
| trichophycin B (17) | smenolactone B (2) | smenolactone C (3) | smenolactone D (4) | |||||
|---|---|---|---|---|---|---|---|---|
| Pos. | δC, type | δH, mult (J in Hz) | δC, type | δH, mult (J in Hz) | δC, type | δH, mult (J in Hz) | δC, type | δH, mult (J in Hz) |
| 1 | 170.9, C | - | 170.9, C | - | 170.9, C | - | 170.9, C | - |
| 2 | 90.3, CH | 5.18, d (1.6) | 90.2, CH | 5.18, d (1.6) | 90.1, CH | 5.18, d (1.6) | 90.2, CH | 5.19, d (1.6) |
| 3 | 176.8, C | - | 176.6, C | - | 176.7, C | - | 176.5, C | - |
| 4a | 31.2, CH2 | 2.65, ddd (17.2, 13.0, 1.7) | 31.2, CH2 | 2.66, ddd (17.1, 13.0, 1.8) | 30.7, CH2 | 2.62, ddd (17.2, 12.9, 1.6) | 31.3, CH2 | 2.68, ddd (17.2, 13.2, 1.7) |
| 4b | 2.32, br. dd (17.1, 3.6) | 2.33, br. d (17.1, 3.6) | 2.34, br. dd (17.2, 3.7) | 2.30, br. dd (17.2, 3.5) | ||||
| 5 | 81.1, CH | 4.32, ddd (13.1, 4.0, 4.0) | 81.1, CH | 4.33, ddd (12.8, 4.0, 4.0) | 82.2, CH | 4.26, ddd (12.8, 5.8, 3.7) | 80.4, CH | 4.35, ddd (13.1, 3.7, 3.7) |
| 6 | 35.1, CH | 1.85 | 35.2, CH | 1.88, m | 35.4, CH | 1.94, ddq (12.1, 6.8, 3.7) | 35.4, CH | 1.93, m |
| 7a | 41.0, CH2 | 1.43, ddd (13.4, 8.0, 5.5) | 41.1, CH2 | 1.47, ddd (13.5, 8.7, 6.2) | 40.5, CH2 | 1.37, ddd (13.3, 10.3, 3.7) | 44.0, CH2 | 2.25, m |
| 7b | 1.08, ddd (13.4, 8.6, 6.1) | 1.11, ddd (13.5, 7.8, 5.5) | 1.18, ddd (13.3, 10.3, 4.0) | 1.93, m | ||||
| 8 | 30.9, CH | 1.49, m | 30.9, CH | 1.54, m | 31.1, CH | 1.51, ddd (6.6, 3.7, 3.7) | 136.2, C | |
| 9a | 32.9, CH2 | 1.27, m | 33.0, CH2 | 1.37, m | 35.2, CH2 | 1.36, ddd (13.6, 12.7, 6.6) | 124.3, CH | 5.25, br. t (7.0) |
| 9b | 1.15, m | 1.23, m | 1.27, m | |||||
| 10a | 35.2, CH2 | 1.37, ddd (13.3, 10.3, 3.7) | 35.2, CH2 | 1.44, ddd (11.7, 9.8, 4.6) | 35.8, CH2 | 1.46, m | 37.2, CH2 | 2.19, m |
| 10b | 1.31, m | 1.41, m | ||||||
| 11 | 70.3, CH | 3.60, tt (7.5, 5.4) | 70.8, CH | 3.75, m | 71.0, CH | 3.76, ddd (12.7, 7.8, 4.4) | 71.1, CH | 3.84, m |
| 12a | 43.1, CH2 | 2.10, ddd (14.3, 4.9, 1.2) | 38.9, CH2 | 2.34, br. dd (13.3, 5.8) | 38.9, CH2 | 2.34, br. dd (13.5, 5.7) | 38.1, CH2 | 2.33, m |
| 12b | 2.09, ddd (14.3, 7.9, 1.2) | 2.24, br. dd (13.3, 7.6) | 2.24, br. dd (13.5, 7.8) | 2.22, m | ||||
| 13 | 141.7, C | 141.5, C | - | 141.7, C | - | 142.1, C | ||
| 14a | 37.0, CH2 | 3.73, br. d (14.5) | 42.8, CH2 | 3.48, br. s | 42.8, CH2 | 3.48, br. s | 42.6, CH2 | 3.48, br. s |
| 14b | 3.54, br. d (14.5) | |||||||
| 15 | 140.5, C | 139.8, C | - | 140.0, C | - | 140.0, C | ||
| 16/20 | 130.1, CH | 7.21, br. d (7.6) | 130.0, CH | 7.19, br. d (7.6) | 130.0, CH | 7.19, br. d (7.4) | 130.1, CH | 7.18, br. d (7.6) |
| 17/19 | 129.7, CH | 7.27, br. t (7.6) | 129.4, CH | 7.29, br. t (7.6) | 129.5, CH | 7.29, br. t (7.4) | 129.5, CH | 7.29, br. t (7.6) |
| 18 | 127.4, CH | 7.19, br. t (7.6) | 127.5, CH | 7.20, br. t (7.6) | 127.5, CH | 7.21, br. t (7.4) | 127.7, CH | 7.20, br. t (7.6) |
| 21 | 115.8, CH | 6.11, br. s | 116.4, CH | 6.05, br. s | 116.4, CH | 6.06, br. s | 116.2, CH | 6.04, br. s |
| 22 | 20.7, CH3 | 0.87, d (6.6) | 20.7, CH3 | 0.90, d (6.6) | 19.6, CH3 | 0.87, d (6.6) | 16.1, CH3 | 1.61, br. s |
| 23 | 15.2, CH3 | 0.98, d (6.8) | 15.2, CH3 | 1.00, d (6.8) | 15.1, CH3 | 0.96, d (6.8) | 14.9, CH3 | 0.92, d (6.8) |
| 24 | 57.0, CH3 | 3.80, s | 57.1, CH3 | 3.80, s | 57.1, CH3 | 3.80, s | 57.4, CH3 | 3.80, s |