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"Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides
Liu, Chen-Fu; Xiong, De-Cai; Ye, Xin-Shan
刊名JOURNAL OF ORGANIC CHEMISTRY
2014-05-16
DOI10.1021/jo500730y
79期:10页:4676-4686
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]STEREOSELECTIVE-SYNTHESIS ; ARYLBORONIC ACIDS ; GLYCOSYLATION ; GLYCALS ; REAGENTS ; SELENOGLYCOSIDES ; BIOSYNTHESIS ; BROMIDE ; DONOR
英文摘要

A new "ring-opening-ring closure" strategy for the synthesis of aryl-C-glycosides was described. This strategy exploited the nickel-catalyzed regioselective beta-O elimination of glycals by reactions with various aryl boronic acids or potassium aryltrifluoroborates to yield the ring-opened products, which underwent the Lewis acid, protonic acid, PhSeCl, or NBS mediated ring closure reactions to afford diverse aryl-C-glycosides. After Lewis acids and protonic acids were screened, it was found that, starting from the ring-opened substrates, the Ph3PHBr or Sc(OTf)(3) mediated ring closure reaction provided alpha-or beta-preferred aryl-C-Delta(2,3)-glycosides, respectively. Furthermore, beta-D-phenyl-C-glycosides were successfully prepared via the PhSeCl-mediated cyclization reaction, whereas the alpha-D-phenyl-C-glycoside was obtained via the NBS-mediated cyclization reaction. After removal of the 2-substituted functionalities by Bu3SnH/AIBN, the synthesis of 2-deoxy-aryl-C-glycosides was ultimately realized in a stereoselective manner.

语种英语
WOS记录号WOS:000336199800045
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/400002259/51740
专题北京大学药学院
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Liu, Chen-Fu,Xiong, De-Cai,Ye, Xin-Shan. "Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(10):4676-4686.
APA Liu, Chen-Fu,Xiong, De-Cai,&Ye, Xin-Shan.(2014)."Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides.JOURNAL OF ORGANIC CHEMISTRY,79(10),4676-4686.
MLA Liu, Chen-Fu,et al.""Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides".JOURNAL OF ORGANIC CHEMISTRY 79.10(2014):4676-4686.
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