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A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides
Wang, Ning; Zhang, Li-He; Ye, Xin-Shan1
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2010
DOI10.1039/b923180c
8期:11页:2639-2649
收录类别SCI ; IC ; CCR
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]NATURALLY-OCCURRING IMINOSUGARS ; LYSOSOMAL ALPHA-GALACTOSIDASE ; RING-CLOSING METATHESIS ; GLYCOSIDASE INHIBITORS ; PHARMACOLOGICAL CHAPERONES ; ASYMMETRIC-SYNTHESIS ; FABRY LYMPHOBLASTS ; SUBSTITUTED AMINES ; GAUCHER-DISEASE ; RATIONAL DESIGN
英文摘要

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted d-lactams. The d-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields.

语种英语
WOS记录号WOS:000277879700024
项目编号973 ; 863
资助机构National Natural Science Foundation of China ; Ministry of Science and Technology of China
引用统计
被引频次:22[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/400002259/57161
专题北京大学药学院
北京大学药学院_药物化学系
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Wang, Ning,Zhang, Li-He,Ye, Xin-Shan. A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2010,8(11):2639-2649.
APA Wang, Ning,Zhang, Li-He,&Ye, Xin-Shan.(2010).A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.ORGANIC & BIOMOLECULAR CHEMISTRY,8(11),2639-2649.
MLA Wang, Ning,et al."A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides".ORGANIC & BIOMOLECULAR CHEMISTRY 8.11(2010):2639-2649.
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