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学科主题: 药学
题名:
Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane
作者: Sang, Yingxia1; Zhao, Jingrui1,2; Jia, Xueshun2; Zhai, Hongbin1,3
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2008-05-02
DOI: 10.1021/jog002425
卷: 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
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/62431
Appears in Collections:北京大学药学院_期刊论文

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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

Recommended Citation:
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.
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