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【结 构 式】 
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【分子编号】45586 【品名】(4bR,4cR,7aR,12bS)-1-chloro-6-methyl-7a,12,12b,13-tetrahydro-4bH-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(4cH,6H)-dione 【CA登记号】577-59-3 |
【 分 子 式 】C21H16ClN3O2 【 分 子 量 】377.82976 【元素组成】C 66.76% H 4.27% Cl 9.38% N 11.12% O 8.47% |
合成路线1
该中间体在本合成路线中的序号：(VI)The Grignard condensation of pyrrolinedione (I) with 7-chloroindol-1-ylmagnesium bromide (II) in toluene gives the monoaddition product (III), which is condensed with indol-1-ylmagnesium bromide (IV) to yield the disubstituted compound (V). The hydrogenation of (V) with H2 over Pd/C in DMF affords the tetrahydro derivative (VI), which is condensed with the aminosugar (VII) in DMF and dehydrogenated with DDQ or DBU to afford the adduct (VIII). Finally, the methylamino group of (VIII) is deprotected by means of TBAF in THF.
| 【1】 Van Vranken, D.L.; Chisholm, J.D.; Regiocontrolled synthesis of the antitumor antibiotic AT2433-A1. J Org Chem 2000, 65, 22, 7541. |
| 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) | 31468 | 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione | C5H3Br2NO2 | 详情 | 详情 | |
| (II) | 45582 | bromo(7-chloro-1H-indol-1-yl)magnesium | C8H5BrClMgN | 详情 | 详情 | |
| (III) | 45583 | 3-bromo-4-(7-chloro-1H-inden-3-yl)-1-methyl-1H-pyrrole-2,5-dione | C14H9BrClNO2 | 详情 | 详情 | |
| (IV) | 45584 | bromo(1H-indol-1-yl)magnesium | C8H6BrMgN | 详情 | 详情 | |
| (V) | 45585 | 3-(7-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione | C21H14ClN3O2 | 详情 | 详情 | |
| (VI) | 45586 | (4bR,4cR,7aR,12bS)-1-chloro-6-methyl-7a,12,12b,13-tetrahydro-4bH-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(4cH,6H)-dione | 577-59-3 | C21H16ClN3O2 | 详情 | 详情 |
| (VII) | 45587 | 2-(trimethylsilyl)ethyl (3S,4S,6S)-4-hydroxy-6-[[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl(methyl)carbamate | C19H37NO10Si | 详情 | 详情 | |
| (VIII) | 45588 | 2-(trimethylsilyl)ethyl (3S,4S,6S)-6-[[(2R,3S,4R,5R,6R)-6-(11-chloro-6-methyl-5,7-dioxo-5,6,7,13-tetrahydro-12H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-12-yl)-4,5-dihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]-4-hydroxytetrahydro-2H-pyran-3-yl(methyl)carbamate | C40H47ClN4O11Si | 详情 | 详情 |