| Synthesis of （2R,3aR,8aR）-6-Chloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization |
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| 引用本文： | 洪文旭,姚祝军.Synthesis of （2R,3aR,8aR）-6-Chloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization[J].中国化学,2004,22(4):365-370. |
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| 作者姓名： | 洪文旭 姚祝军 |
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| 作者单位： | StateKeyLaboratoryofBioorganicandNaturalProductsChemistry,ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciences,Shanghai200032,China |
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| 基金项目： | theMajorStateBasicResearchandDevelopmentProgramofChina(No.G2000077500)，theNationalNaturalScienceFounda-tionofChina(No.20172061)，theChineseAcademyofSciences，andtheShanghaiMunicipalCommissionofScienceandTechnology. |
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| 摘 要： | A synthesis of (2R，3aR，8aR)-6-chloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo2,3-b]indole-2-carboxylic acid methyl ester (1) was achieved. An aldol reaction with Garner aldehyde, a hydroxyl introduction by Davis reagent, and a reductive intramolecular ring-closure reaction were served as the key steps. This piece of work provides a new way to synthesize the analogues of hexahydropyrrolo2,3-b]indole, starting from readily available chemical substrates and inexpensive reagents.
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| 关 键 词： | 醛醇缩合反应 Davis氧化 还原闭环反应 吲哚衍生物 抗癌性 （2R 3aR 8aR）-6-氯-3a-羟基-1 2 3 3a 8 8a-六氢吡咯[2 3-b]吲哚-2-羧基甲酯酸 |
Synthesis of (2R,3aR,8aR)-6-Chloro-3a-hydroxy-1,2,3,3a,8,8a- hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization |
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| HONG,Wen-Xu YAO,Zhu-Jun State Key Laboratory of Bioorganic and Natural Products Chemistry.Synthesis of (2R,3aR,8aR)-6-Chloro-3a-hydroxy-1,2,3,3a,8,8a- hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization[J].Chinese Journal of Chemistry,2004,22(4):365-370. |
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| Authors: | HONG Wen-Xu YAO Zhu-Jun State Key Laboratory of Bioorganic and Natural Products Chemistry |
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| Institution: | HONG,Wen-Xu YAO,Zhu-Jun* State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China |
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| Abstract: | A synthesis of (2R,3aR,8aR)-6-chloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo2,3-b]indole-2-carboxylic acid methyl ester (1) was achieved. An aldol reaction with Garner aldehyde, a hydroxyl introduction by Davis re-agent, and a reductive intramolecular ring-closure reaction were served as the key steps. This piece of work pro-vides a new way to synthesize the analogues of hexahydropyrrolo2,3-b]indole, starting from readily available chemical substrates and inexpensive reagents. |
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| Keywords: | aldol reaction Davis oxidation reductive ring-closure reaction indole derivative anticancer activity |
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