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【结 构 式】 
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【分子编号】42038 【品名】methyl (1S,7R)-1-(bromomethyl)-5-hydroxy-7-methyl-8-oxo-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydrocyclopenta[e]indole-7-carboxylate 【CA登记号】 |
【 分 子 式 】C27H27BrN2O8 【 分 子 量 】587.42406 【元素组成】C 55.21% H 4.63% Br 13.6% N 4.77% O 21.79% |
合成路线1
该中间体在本合成路线中的序号：(I)The acylation of duocarmicin B2 (I) with 4-methylpiperazin-1-ylcarbonyl chloride (II) by means of pyridine in dichloromethane gives the carbamate (III), which is reduced with NaBH4 in methanol as the better solvent, to yield the secondary alcohol (IV). Finally, this compound is submitted to a Wagner-Meerwein rearrangement in acidic medium. CSA, TsOH, MsOH, TfOH and BF3.Et2O have been tested with similar yields and hot 1,2-dichloroethane and toluene have been used as solvents.
| 【1】 Masuda, Y.; Kasai, M.; Saito, H.; Sakaguchi, A.; Kinugawa, M.; Nagamura, S.; Ogasa, T.; Practical synthesis of the high-quality antitumor agent KW-2189 from duocarmycin B2 using a facile one-pot synthesis of an intermediate. Org Process Res Dev 1998, 2, 6, 344. |
| 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) | 42038 | methyl (1S,7R)-1-(bromomethyl)-5-hydroxy-7-methyl-8-oxo-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydrocyclopenta[e]indole-7-carboxylate | C27H27BrN2O8 | 详情 | 详情 | |
| (II) | 30370 | 4-methyl-1-piperazinecarbonyl chloride | C6H11ClN2O | 详情 | 详情 | |
| (III) | 42039 | methyl (1S,7R)-1-(bromomethyl)-7-methyl-5-[[(4-methyl-1-piperazinyl)carbonyl]oxy]-8-oxo-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydrocyclopenta[e]indole-7-carboxylate | C33H37BrN4O9 | 详情 | 详情 | |
| (IV) | 42040 | methyl (1S,7R)-1-(bromomethyl)-8-hydroxy-7-methyl-5-[[(4-methyl-1-piperazinyl)carbonyl]oxy]-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydrocyclopenta[e]indole-7-carboxylate | C33H39BrN4O9 | 详情 | 详情 |