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学科主题: 药学
题名:
"Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides
作者: Liu, Chen-Fu; Xiong, De-Cai; Ye, Xin-Shan
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2014-05-16
DOI: 10.1021/jo500730y
卷: 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
所属项目编号: 2012CB822100 ; 2013CB910700 ; 2012ZX09502001-001 ; 21232002 ; YETP0063
项目资助者: Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Beijing Higher Education Young Elite Teacher Project
WOS记录号: WOS:000336199800045
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/51740
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

Recommended Citation:
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.
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