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Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane
Sang, Yingxia1; Zhao, Jingrui1,2; Jia, Xueshun2; Zhai, Hongbin1,3
刊名JOURNAL OF ORGANIC CHEMISTRY
2008-05-02
DOI10.1021/jog002425
73期:9页:3589-3592
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]CONFORMATIONALLY RESTRICTED ANALOGS ; NEURONAL NICOTINIC RECEPTORS ; RING-CLOSING METATHESIS ; ENANTIOSPECIFIC SYNTHESIS ; GLUTAMIC ACID ; DERIVATIVES ; CYCLOADDITION ; (S)-NICOTINE ; PYRROLIDINE ; EPIBATIDINE
英文摘要

(+)-Pyrido[3,4-b]homotropane (PHT) was efficiently constructed in 12 steps from N,N-diisopropylisonicotinamide. The synthesis features (i) RCM reaction in installing the homotropane skeleton, (ii) Snieckus ortho-lithiation of N,N-diisopropylisonicotinamide followed by acylation, (iii) Myer reduction of bulky tertiary amide to alcohol with LiBH(3)NH(2), and (iv) utilization of L-glutamic acid to introduce and establish the requisite stereogenic centers.

语种英语
WOS记录号WOS:000255339600041
引用统计
被引频次:12[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/62431
专题北京大学药学院
作者单位1.Shanghai Univ, Dept Chem, Shanghai 200436, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China
3.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
推荐引用方式
GB/T 7714
Sang, Yingxia,Zhao, Jingrui,Jia, Xueshun,et al. Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane[J]. JOURNAL OF ORGANIC CHEMISTRY,2008,73(9):3589-3592.
APA Sang, Yingxia,Zhao, Jingrui,Jia, Xueshun,&Zhai, Hongbin.(2008).Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane.JOURNAL OF ORGANIC CHEMISTRY,73(9),3589-3592.
MLA Sang, Yingxia,et al."Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane".JOURNAL OF ORGANIC CHEMISTRY 73.9(2008):3589-3592.
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