Table XII.
1H NMR Data of Homolycorine-Type Compounds: Lactone Alkaloids
| Alkaloid | 26 | 27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 40 |
|---|---|---|---|---|---|---|---|---|---|---|
| H-1 | 4.81 ddd | 4.78 m | 4.86 br d | 4.80 ddd | 4.75 m | 4.85 s | 4.59 br d | 4.63 dd | 4.58 br s | 4.83 m |
| H-2 (2H) | 2.49 m | 2.59 m | 2.5–2.7 m | 2.51 m | 2.60 m | 2.62 m | 4.28 br t (Hβ) | 5.46 dd (Hβ) | 4.38 br s (Hβ) | 2.64 m |
| H-3 | 5.50 m | 5.50 d | 5.63 br d | 5.55 m | 5.50 br d | 5.64 m | 5.68 br s | 5.62 m | 5.63 br s | 5.76 br d |
| H-4a | 2.72 dd | 2.73 dd | 2.96 br d | 2.71 br d | 2.74 m | 5.50 br d | 2.66 br d | 2.74 br d | 2.62 d | 3.87 br d |
| H-7 | 7.57 s | 7.60 s | 7.47 s | 7.54 s | 7.49 s | 7.52 s | 7.47 s | 7.52 s | 7.45 s | 7.44 s |
| H-10 | 6.99 s | 6.98 s | 7.13 s | 6.91 s | 6.96 s | 7.11 s | 6.95 s | 6.97 s | 6.92 s | 7.24 s |
| H-10b | 2.64 dd | 2.63 dd | 2.86 dd | 2.60 dd | 2.74 m | 2.66 d | 2.83 dd | 2.79 br d | 2.85 dd | 3.50 dd |
| H-11 (2H) | 2.6–2.7 m | 2.50 m | 2.5–2.7 m | 2.5–2.6 m | 2.50 m | 2.52 m | 2.5–2.6 m | 2.5–2.7 m | 2.48 m | 3.57 m |
| H-12α | 3.14 ddd | 3.14 ddd | 3.31 ddd | 3.15 ddd | 3.18 ddd | 3.15 ddd | 3.17 ddd | 3.19 ddd | 3.13 ddd | 2.88 m |
| H-12β | 2.24 ddd | 2.25 dd | 2.45 dd | 2.30 ddd | 2.27 dd | 2.89 dd | 2.31 dd | 2.37 dd | 2.23 ddd | 2.72 m |
| OCH2O | — | — | — | — | 6.07 (2d) | 6.05 d | — | — | 6.04 (2d) | — |
| OMe | 3.96 s | 3.95 s | 3.97 s | 3.94 s | — | — | 3.95 s | 3.94 s | — | 3.96 s |
| OMe | 3.95 s | — | — | — | — | — | — | — | — | — |
| NMe | 2.00 s | 2.00 s | 2.16 s | 2.01 s | 2.06 s | — | 2.08 s | 2.06 s | 2.03 s | 2.94 s |
| OAc | — | — | 2.00 s | — | — | — | — | 2.00 s | — | — |
| CHA | — | — | — | — | — | — | — | 2.53 dd | — | — |
| CHB | — | — | — | — | — | — | — | 2.65 dd | — | — |
| CHOH | — | — | — | — | — | — | — | 5.24 m | — | — |
| Me | — | — | — | — | — | — | — | 1.29 d | — | — |
| Solvent | d | d | b | b | d | d | b | b | d | b |
| MHz | 200 | 400 | 250 | 200 | 400 | 400 | 200 | 400 | 500 | 200 |
| Reference | (82) | (324) | (70) | (82) | (165) | (165) | (138) | (72) | (71) | (137) |
| Solvent a: DMSO-d6, b: CDC13-CDC3OD, c: CD3OD, d: CDCl3 | ||||||||||
| Alkaloid | 35 | 36 | 37 | 38 | 39 |
|---|---|---|---|---|---|
| H-1α | 4.35 br d | 4.29 br d | 4.35 d | 4.17 d | 4.15 br s |
| H-2α | 2.35 m | 2.35 m | 2.31 dm | 2.26 dd | — |
| H-2β | 2.65 m | 2.65 m | 2.62 dm | 2.53 dm | 4.21 br s |
| H-3 | 5.50 br s | 5.50 br d | 5.46 br d | 5.39 br s | 5.69 br s |
| H-4a | 2.78 br d | 2.77 dd | 2.72 br d | 2.69 br d | 2.87 d |
| H-6β | 5.93 s | 5.54 s | 5.99 s | 5.39 br s | 5.43 s |
| H-7 | 6.93 s | 6.80 s | 6.85 s | 6.67 s | 6.73 s |
| H-10 | 6.99 s | 6.93 s | 6.90 s | 6.77 s | 6.94 s |
| H-10b | 2.44 dd | 2.44 dd | 2.4–2.5 m | 2.35 dd | 2.85 d |
| H-11 (2H) | 2.4–2.6 m | 2.4–2.6 m | 2.4–2.5 m | 2.3–2.4 m | 2.54 m |
| H-12α | 3.15 ddd | 3.15 ddd | 3.14 ddd | 3.08 dd | 3.33 m |
| H-12β | 2.27 dd | 2.23 dd | 2.25 dd | 2.17 dd | 2.38 dt |
| OCH2O | — | — | 5.97 d | 5.83 d | 5.91 (2d) |
| OMe | 3.88 s | 3.89 s | — | 3.43 s | 3.51 s |
| OMe | 3.87 s | 3.88 s | — | — | — |
| OMe | — | 3.55 s | — | — | — |
| NMe | 2.08 s | 2.10 s | 2.11 s | 2.05 s | 2.22 s |
| Solvent | c | d | d | d | d |
| MHz | 250 | 200 | 400 | 400 | 500 |
| Reference | (106) | (104) | (165) | (165) | (71) |
Solvent a, DMSO-d6; b, CDCl3-CD3OD; c, CD3OD; d, CDCl3.