|
【结 构 式】 
|
【分子编号】63642 【品名】7-methyl 3-[(4-nitrophenyl)methyl] 7-{4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-5-[(methyloxy)carbonyl]-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl}-5-[2-hydroxy-2-(hydroxymethyl)butyl]-1,4,5,6,7,8-hexahydroazoni 【CA登记号】 |
【 分 子 式 】C54H65N5O14 【 分 子 量 】1008.1354 【元素组成】C 64.34% H 6.5% N 6.95% O 22.22% |
合成路线1
该中间体在本合成路线中的序号：(XXII)The tetracyclic intermediate (X) is coupled to vindoline (XX) upon treatment with p-nitrobenzyl chloroformate to furnish the bis-indole adduct (XXI) as a mixture of epimers at the carbomethoxy group. Isolation of the desired isomer, followed by acidic ketal hydrolysis leads to diol (XXII). This is then oxidized to the alpha-hydroxy aldehyde (XXIII) with SO3-pyridine in DMSO. Finally, hydrogenolysis of the p-nitrobenzyl carbamate, with concomitant intramolecular reductive amination of the aldehyde group produces the title bis-indole alkaloid
| 【1】 Magnus, P.; Mendoza, J.S.; Stamford, A.; Ladlow, M.; Willis, P.; Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analogue: Solvent effect on the stereochemistry of the crucial C-15/C-18' bond. J Am Chem Soc 1992, 114, 26, 10232. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 63633 | methyl 2-[(2-ethyl-1,4-dioxaspiro[4.5]dec-2-yl)methyl]-2,3,6,11-tetrahydro-1H-indolizino[8,7-b]indole-11b(5H)-carboxylate | C27H36N2O4 | 详情 | 详情 | |
| (XX) | 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 | |
| (XXI) | 63641 | 7-methyl 3-[(4-nitrophenyl)methyl] 7-{4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-5-[(methyloxy)carbonyl]-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl}-5-[(2-ethyl-1,4-dioxaspiro[4.5]dec-2-yl)methyl]-1,4,5,6,7,8-hex | C60H73N5O14 | 详情 | 详情 | |
| (XXII) | 63642 | 7-methyl 3-[(4-nitrophenyl)methyl] 7-{4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-5-[(methyloxy)carbonyl]-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl}-5-[2-hydroxy-2-(hydroxymethyl)butyl]-1,4,5,6,7,8-hexahydroazoni | C54H65N5O14 | 详情 | 详情 | |
| (XXIII) | 63643 | 7-methyl 3-[(4-nitrophenyl)methyl] 7-{4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-5-[(methyloxy)carbonyl]-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl}-5-(2-formyl-2-hydroxybutyl)-1,4,5,6,7,8-hexahydroazonino[5,4-b] | C54H63N5O14 | 详情 | 详情 |