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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

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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摘要 A 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 (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 hexahydropyrrolo[2,3-b]indole, starting from readily available chemical substrates and inexpensive reagents. A 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 (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 hexahydropyrrolo[2,3-b]indole, starting from readily available chemical substrates and inexpensive reagents.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2004年第4期365-370,共6页 中国化学(英文版)
基金 theMajorStateBasicResearchandDevelopmentProgramofChina(No.G2000077500) theNationalNaturalScienceFounda-tionofChina(No.20172061) theChineseAcademyofSciences andtheShanghaiMunicipalCommissionofScienceandTechnology.
关键词 aldol reaction Davis oxidation reductive ring-closure reaction indole derivative anticancer activity aldol reaction, Davis oxidation, reductive ring-closure reaction, indole derivative, anticancer activity
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