|
【结 构 式】 
|
【分子编号】63597 【品名】(13S,15R)-13-[(3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-5-(methoxycarbonyl)-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl]-17-ethyl-13-(methoxycarbonyl)-11-aza-1-azoniatetracyclo[13.3.1.0~4,12~.0~5,10~]nonadeca-1(18),4(12),5,7,9,16-hexaene 【CA登记号】 |
【 分 子 式 】C48H55F3N4O10 【 分 子 量 】904.9808696 【元素组成】C 63.71% H 6.13% F 6.3% N 6.19% O 17.68% |
合成路线1
该中间体在本合成路线中的序号：(III)In a similar procedure, coupling of catharanthine-N-oxide (I) with vindoline (II) under Polonovski reaction conditions leads to the iminium salt (III). This is subsequently converted into the desired enamine (IV) employing NADH as the reducing reagent. Aeration of enamine (IV) in the presence of FeCl3, followed by reductive work up leads to the title compound (4).
| 【1】 Kutney, J.P.; Choi, L.S.L.; Nakano, J.; Tsukamoto, H.; McHugh, M.; Boulet, C.A.; A highly efficient and commercially important synthesis of the antitumor Catharantus alkaloids vinblastine and leurosidine from catharanthine and vindoline. Heterocycles 1988, 27, 8, 1845. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 63595 | (1R,15R,18R)-17-ethyl-1-(methoxycarbonyl)-3-aza-13-azoniapentacyclo[13.3.1.0~2,10~.0~4,9~.0~13,18~]nonadeca-2(10),4,6,8,16-pentaen-13-olate | C21H24N2O3 | 详情 | 详情 | |
| (II) | 63596 | methyl 4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | C25H32N2O6 | 详情 | 详情 | |
| (III) | 63597 | (13S,15R)-13-[(3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-5-(methoxycarbonyl)-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl]-17-ethyl-13-(methoxycarbonyl)-11-aza-1-azoniatetracyclo[13.3.1.0~4,12~.0~5,10~]nonadeca-1(18),4(12),5,7,9,16-hexaene | C48H55F3N4O10 | 详情 | 详情 | |
| (IV) | 63601 | methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(13S,15S)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0~4,12~.0~5,10~]nonadeca-4(12),5,7,9,17-pentaen-13-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | C46H56N4O8 | 详情 | 详情 |