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An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings

文献类型：期刊论文

作者Luo, Wen4,5; Cheng, Xinqiang4; Zhu, Xinyuan1,4; Li, Yong4,5; Liu, Yongjia2,3; Huang, Wenqian2,3; Li, Yan3; Zhao, Guilong1,2,3,4,5
刊名SYNTHETIC COMMUNICATIONS
出版日期2023-11-18
页码10
ISSN号0039-7911
关键词Diels-Alder cycloaddition bridged bicyclic ring S(N)2 alkylation gamma-aminobutyric acid (GABA) stereochemistry
DOI10.1080/00397911.2023.2284348
通讯作者Zhao, Guilong(zhao_guilong@126.com)
英文摘要An efficient, concise 5-step synthetic approach to gamma-aminobutyric acid (GABA) derivatives bearing bridged bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings was developed, which consists of Diels-Alder cycloaddition to construct the bridged bicyclic rings with a nitrile functionality, hydrogenation, LDA-mediated SN2 alkylation to introduce acetate moiety at the alpha-position of nitrile, reduction of the nitrile functionality to amino group followed by intramolecular formation of lactam and finally acidic hydrolysis of lactam to give the desired GABA derivatives (1 and 19 as HBr salts). The reaction conditions of Diels-Alder cycloaddition and LDA-mediated SN2 alkylation were intensively optimized to improve the yields. The stereochemistry of the SN2 reaction involved in the bicyclo[2.2.1]heptane ring system was unambiguously elucidated by single-crystal X-ray diffraction. This synthetic approach possesses advantages of less reaction steps, high overall yields and avoidance of toxic reagents, and may find wide applications in the synthesis of other GABA derivatives with similar bicyclic or polycyclic rings. [GRAPHICS]
资助项目The authors want to thank Ms Xiaotong Lin and Ms Yanlan Qin for performing NMR and HR-MS determinations, respectively.
WOS研究方向Chemistry
语种英语
出版者TAYLOR & FRANCIS INC
WOS记录号WOS:001108027800001
源URL[http://119.78.100.183/handle/2S10ELR8/308164]  
专题中国科学院上海药物研究所
通讯作者Zhao, Guilong
作者单位1.China Pharmaceut Univ, Sch Pharm, Nanjing, Peoples R China
2.Univ Chinese Acad Sci, Sch Pharm, Beijing, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai, Peoples R China
4.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
5.Southern Med Univ, Sch Pharmaceut Sci, Guangzhou, Peoples R China
推荐引用方式
GB/T 7714		 Luo, Wen,Cheng, Xinqiang,Zhu, Xinyuan,et al. An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings[J]. SYNTHETIC COMMUNICATIONS,2023:10.
APA Luo, Wen.,Cheng, Xinqiang.,Zhu, Xinyuan.,Li, Yong.,Liu, Yongjia.,...&Zhao, Guilong.(2023).An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings.SYNTHETIC COMMUNICATIONS,10.
MLA Luo, Wen,et al."An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings".SYNTHETIC COMMUNICATIONS (2023):10.

入库方式： OAI收割

来源：上海药物研究所

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