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

作     者：洪文旭 姚祝军 

作者机构：State Key Laboratory of Bioorganic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2004年第22卷第4期

页      面：365-370页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：theMajorStateBasicResearchandDevelopmentProgramofChina(No.G2000077500) theNationalNaturalScienceFounda-tionofChina(No.20172061) theChineseAcademyofSciences andtheShanghaiMunicipalCommissionofScienceandTechnology 

主　　题：aldol reaction Davis oxidation reductive ring-closure reaction indole derivative anticancer activity 

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.