Table 1.
NMR data for 1E-pitiamide B (1) and 1Z-pitiamide B (2) in CDCl3 (600 MHz)
| Position | 1E-pitiamide B (1) | 1Z-pitiamide B (2) | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|
|
|
||||||||||
| δH mult. ( J in Hz) | δCa | COSY | HMBC | TOCSY | δH mult. ( J in Hz) | δCa | COSY | HMBC | TOCSY | |
| 1 | 6.08 d (13.1) | 118.5 | 2 | 2, 3 | 2, 3, 4, 5, 6, 7, 8, 9 | 5.88 d (7.0) | 116.22 | 2 | 2, 3, ( 5, 6) | 2, 3 |
| 2 | 6.4 dd (13.1, 10.8) | 133.7 | 1, 3 | 1, 3 | 1, 3, 4, 5, 6, 7 | 6.25 dd (10.3, 7.0) | 129.9 | 1, 3 | 1, 4 | 3, 4, 5, 6, 7, 8 |
| 3 | 5.96 dd (15.2, 10.8) | 126.4 | 2, 4, 5 | 1, 2, 4, 5, 6, 7, 8, 9 | 6.43 ddd (15.3, 10.3, 1.1) | 124.0 | 2, 4, 5 | 1, 2, 5 | 1, 2, 5, 6, 7, 8, 9 | |
| 4 | 5.68 dt (15.2, 7.1) | 135.8 | 3, 5 | 2, 6 | 1, 2, 3, 5, 6, 7, 8, 11a, 11b, 24 | 5.84 dt (15.3, 7.0) | 138.5 | 3, 5 | 2, 5, 6 | 2, 3, 5, 6, 7, 8, 9 |
| 5 | 2.07 m | 32.5 | 4, 6 | 3, 4, 6 | 1, 2, 3, 4, 6, 7, 8 | 2.14 dt (7.5, 7.5) | 32.8 | 3, 4, 6 | 3, 4, 6 | 2, 3, 4, 6, 7, 8, 9 |
| 6 | 1.39 m | 28.9 | 5, 7 | 4, 5 | 3, 4, 5, 7, 8, 9 | 1.42 m | 28.9 | 5, 7 | 4, 5, 8 | 2, 3, 4, 5, 7, 8, 9 |
| 7 | 1.29 m | 29 | 6, 8 | 8 | 3, 4, 5, 6, 8, 9 | 1.29 m | 29.0 | 6, 8 | 5, 8, 9 | 2, 3, 4, 5, 6, 8, 9 |
| 8 | 1.57 m | 23.7 | 7, 9 | 7, 9, 10 | 3, 4, 5, 6, 7, 9 | 1.57 m | 23.7 | 7, 9 | 7, 9, 10 | 2, 3, 4, 5, 6, 7, 9 |
| 9 | 2.38 t (7.4) | 43.8 | 8 | 7, 8, 10 | 6, 7, 8, 12 | 2.38 t (7.4) | 43.8 | 8 | 7, 8, 10 | 4, 6, 7, 8, 12 |
| 10 | 211.2 | 211.2 | ||||||||
| 11a | 2.39 dd (17.0, 7.0) | 49.7 | 11b, 12 | 10 | 11b, 12, 13a, 13b, 14a, 14b, 15, 24 | 2.39 dd (17.0, 7.0) | 49.7 | 11b, 12 | 10, 12, 13, 24 | 11b, 12, 13a, 13b, 14a, 14b, 15, 24 |
| 11b | 2.30 dd (17.0, 7.0) | 49.7 | 11a, 12, | 10 | 11a, 12, 13a, 13b, 14a, 14b, 15, 24 | 2.30 dd (17.0, 7.0) | 49.7 | 11a, 12 | 10, 12, 13, 24 | 11a, 12, 13a, 13b, 14a, 14b, 15, 24 |
| 12 | 2.06 m | 26.5 | 11a, 11b, 13a, 13b, 24 | 24 | 11a, 11b, 14a, 14b, 24 | 2.06 m | 26.5 | 11a, 11b,13a, 13b, 24 | 11, 13, 24 | 11a, 11b, 13a, 13b, 14a, 14b, 15, 24 |
| 13a | 1.43 m | 36.5 | 12, 13b, 14a, 14b | 24 | 13b, 14a, 14b, 24 | 1.43 m | 36.5 | 12, 13b, 14a, 14b | 11, 12, 14, 24 | 11b, 12, 13b, 14a, 14b, 15, 24 |
| 13b | 1.37 m | 36.5 | 12, 13a, 14a, 14b | 24 | 13a, 14a, 14b, 25 | 1.37 m | 36.5 | 13a, 14a, 14b | 11, 12, 14, 24 | 11b, 12, 13a, 14a, 14b, 15, 24 |
| 14a | 3.28 m | 37.4 | 13a, 13b, 14b, 15 | 11a, 11b, 12, 13a, 13b, 14b, 15, 24 | 3.28 m | 37.4 | 13a, 13b, 14b, 15 | 12, 13 | 11a, 11b, 12, 13a, 13b, 14b, 15, 24 | |
| 14b | 3.18 m | 37.4 | 13a, 13b, 14a, 15 | 11a, 11b, 12, 13a, 13b, 14a, 15, 24 | 3.18 m | 37.4 | 13a, 13b, 14a, 15 | 12 | 11a, 11b, 12, 13a, 13b, 14a, 15, 24 | |
| 15 | 5.66 | 14a, 14b | 14a, 14b | 5.68 br s | 14a, 14b | 12, 13a, 13b, 14a, 14b, 24 | ||||
| 16 | 173.0 | 173.0 | ||||||||
| 17 | 2.24 t (7.6) | 36.8 | 18 | 16, 18, 19 | 18, 19, 20, 21 | 2.24 t (7.6) | 36.8 | 18 | 18, 19, 20, 21 | |
| 18 | 2.32 m | 28.8 | 17, 19 | 16, 17, 20 | 17, 19, 20, 21 | 2.32 m | 28.8 | 17, 19 | 16, 17, 19, 20 | 17, 19, 20, 21 |
| 19 | 5.40 dt (15.2, 6.6) | 128.6 | 18, 20 | 17, 18, 20, 21, 22, 23 | 5.40 dt (15.2, 6.7) | 128.6 | 18, 20 | 18, 21 | 17, 18, 20, 21, 22, 23 | |
| 20 | 5.47 dt (15.2, 6.6) | 131.8 | 19, 21 | 17, 18, 19, 21, 22, 23 | 5.47 dt (15.2, 6.7) | 131.8 | 19, 21 | 18 | 17, 18, 19, 21, 22, 23 | |
| 21 | 1.95 dt (7.3, 7.2) | 34.8 | 20, 22 | 20, 19, 22, 23 | 17, 18, 19, 20, 22, 23 | 1.95 dt (7.3, 7.2) | 34.8 | 20, 22 | 19, 20, 22, 23 | 17, 18, 19, 20, 22, 23 |
| 22 | 1.34 m | 22.5 | 21, 23 | 20, 21, 23 | 19, 20, 21, 23 | 1.34 m | 22.5 | 21, 23 | 20, 21, 23 | 19, 20, 21, 23 |
| 23 | 0.87 t (7.3) | 13.8 | 22 | 21, 22 | 17, 18, 19, 20, 21, 22 | 0.87 t (7.3) | 13.8 | 22 | 21, 22 | 17, 18, 19, 20, 21, 22 |
| 24 | 0.92 d (6.7) | 20.2 | 12 | 11, 12, 13 | 11a, 11b, 12, 13a, 13b, 14a, 14b, 15 | 0.92 d (6.7) | 20.2 | 12 | 11, 13, 12 | 11a, 11b, 12, 13a, 13b, 14a, 14b, 15 |
a
Deduced from HSQC and HMBC experiments