Table XI.
1H NMR Data of Lycorine-Type Alkaloids
| Alkaloid | 1 | 3 | 4 | 5 | 6 | 7 | 10 | 13 | 14 | 15 | 19 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| H-1 | 4.27 br s | 4.85 br s | 5.58 m | 4.43 t | 4.53 dd | 4.55 s | 4.70 m | 4.26 dd | 5.54 dd | 5.51 m | 4.37 q |
| H-2α | 3.97 br s | 4.50 t | 4.15 dd | 5.29 dd | 4.18 m | 3.72 m | 2.59 m | 2.3–2.6 m | 2.3–2.5 m | 2.36 m | 2.46 ddd |
| H-2β | — | — | — | — | — | — | 2.59 m | 2.3–2.4 m | 2.3–2.5 m | 2.36 m | 2.34 dddd |
| H-3 | 5.37 br s | 5.60 t | 5.69 dd | 5.45 t | 5.55 m | 5.55 br s | 5.41 m | 5.54 br d | 5.39 br s | 5.32 br t | 5.87 br dt |
| H-4a | 2.60 d | 3.02 br d | 2.90 br s | 2.85 d | 2.87 dd | 2.65 s | 2.78 dd | 2.70 br d | 2.3–2.5 m | 2.2–2.3 m | 4.24 br d |
| H-6α | 3.32 d | 3.68 br d | 3.61 dd | 3.54 d | 3.55 dd | 3.40 br d | 3.52 dd | 3.31 d | 3.54 br d | 3.5–3.6 br s | 4.40 d |
| H-6β | 4.02 d | 4.16 d | 4.17 d | 4.14 d | 4.16 d | 4.05 d | 4.13 d | 3.93 d | 3.59 br d | 3.5–3.6 br s | 4.61 dt |
| H-7 | 6.68 s | 6.71 s | 6.70 s | 6.61 s | 6.75 s | 6.52 s | 6.58 s | 6.59 s | 6.64 s | 6.71 s | 6.60 s |
| H-10 | 6.81 s | 6.89 s | 6.74 s | 6.83 s | 6.96 s | 6.78 s | 6.82 s | 6.82 s | 7.08 s | 7.14 br s | 7.08 s |
| H-10b | 2.50 m | 2.74 br d | 2.90 br s | 2.69 d | 2.76 ddd | 2.65 s | 2.41 ddd | 2.98 dd | 3.33 dd | 3.27 dd | 3.52 dd |
| H-11 (2H) | 2.44 m | 2.6–2.7 m | 2.66 t | 2.63 m | 2.64 m | 2.4–2.6 m | 2.59 m | 2.5–2.6 m | 2.3–2.5 m | 2.2–2.4 m | 2.8–2.9 m |
| H-12α | 2.19 ddd | 2.6–2.7 m | 2.59 br t | 2.42 dt | 2.42 br q | 2.25 dd | 2.33 br q | 2.3–2.4 m | 2.79 m | 2.6–2.8 m | 3.71 ddd |
| H-12β | 3.19 dd | 3.37 dd | 3.33 m | 3.35 dt | 3.35 ddd | 3.25 ddd | 3.32 ddd | 3.32 m | 2.79 m | 2.6–2.8 m | 3.83 ddd |
| OCH2O | 5.95 s | — | — | — | — | — | 5.91 (2d) | — | — | — | — |
| OMe | — | 3.84 s | 3.84 s | 3.82 s | 3.85 s | 3.78 s | — | 3.89 s | 3.86 s | 3.74 s | 3.87 s |
| OMe | — | — | — | — | 3.80 s | 3.74 s | — | — | — | — | — |
| OMe | — | — | — | — | — | 3.40 s | — | — | — | — | — |
| OAc | — | — | 1.92 s | 2.06 s | — | — | — | — | 1.98 s | 2.23 s | — |
| OAc | — | — | — | — | — | — | — | — | — | 1.92 s | — |
| Solvent | a | b | b | b | c | d | d | d | d | d | c |
| MHz | 300 | 200 | 200 | 200 | 270 | 200 | 270 | 400 | 400 | 400 | 500 |
| Reference | (298) | (113) | (113) | (113) | (303) | (135) | (305) | (167) | (167) | (167) | (316) |
| Solvent a: DMSO-d6, b: CDC13-CDC3OD, c: CD3OD, d: CDCl3 | |||||||||||
| Alkaloid | 20 | 21 | 22 | 23 | 24 |
|---|---|---|---|---|---|
| H-1 | 7.31 dd | 7.85 br d | 8.32 d | 8.13 d | 7.54 s |
| H-2 | 6.75 t | 7.27 t | 7.84 t | — | — |
| H-3 | 6.99 dt | 7.33 br d | 7.70 d | 7.59 br s | 7.34 s |
| H-6 | 4.09 s | — | 10.42 s | 9.55 s | 9.19 s |
| H-7 | 6.64 s | 7.57 s | 8.09 s | 7.92 s | 7.59 s |
| H-10 | 7.17 s | 7.81 s | 7.86 s | 8.34 s | 7.88 s |
| H-11 (2H) | 3.00 br t | 3.45 br t | 3.76 t | 3.88 t | 3.70 t |
| H-12 (2H) | 3.32 t | 4.45 br t | 5.42 t | 5.35 t | 5.12 t |
| OMe | 3.93 s | 4.09 s | 4.19 s | 4.33 s | — |
| OMe | 3.87 s | 4.03 s | 4.08 s | 4.20 s | — |
| OMe | — | — | — | 4.17 s | — |
| OCH2O | — | — | — | — | 6.32 s |
| Solvent | d | b | b | c | e |
| MHz | 200 | 200 | 500 | 500 | 600 |
| Reference | (114) | (114) | (71) | (68) | (320) |
| Solvent a: DMSO-d6, b: CDC13-CDC3OD, c: CD3OD, d: CDCl3, e: D2O+0.01% | |||||
| Alkaloid | 16 | 17 | 25 |
|---|---|---|---|
| H-1α | — | — | 2.85 ddd |
| H-1β | 4.66 m | 4.69 br s | 3.13 dd |
| H-2α | 3.4–4.2 m | 3.69 m | 1.8–1.95 m |
| H-2β | — | — | 2.25–2.4 m |
| H-3α | — | — | 1.38 qd |
| H-3β | 4.66 m | 4.60 br s | 2.25–2.4 m |
| H-4 | — | — | 3.4–3.5 m |
| H-4a | 3.4–4.2 m | 4.09 m | — |
| H-6α | 3.54 d | 3.69 m | 9.50 s (1H) |
| H-6β | 4.09 d | 4.15 br d | |
| H-7 | 6.68 s | 6.78 s | 6.95 s |
| H-10 | 6.88 s | 6.93 s | — |
| H-10b | 2.70 d | 2.84 br d | — |
| H-11α | 5.56 br s (1H) | 5.75 br d (1H) | 2.05 ddd |
| H-11β | 2.70 dt | ||
| H-12α | 3.4–4.2 m (2H) | 3.69 m | 4.75–4.95 m (2H) |
| H-12β | 4.15 br d | ||
| OMe | 3.86 s | — | 4.15 s |
| OMe | 3.82 s | — | 4.05 s |
| OMe | 3.44 s | 3.44 s | 3.90 s |
| OCH2O | — | 5.92 br s | — |
| Solvent | d | c | d |
| MHz | 400 | 600 | 250 |
| Reference | (313) | (173) | (67) |
Solvent a: DMSO-d6, b: CDCl3-CD3OD, c: CD3OD, d: CDCl3, e: D2O+0.01% TFA-d1.