"Ring Opening-Ring Closure" Strategy for the Synthesis of Aryl-C-glycosides

被引：44

作者：

Liu, Chen-Fu ^{[1
]}

Xiong, De-Cai ^{[1
]}

Ye, Xin-Shan ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 10期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE-SYNTHESIS; ARYLBORONIC ACIDS; GLYCOSYLATION; GLYCALS; REAGENTS; SELENOGLYCOSIDES; BIOSYNTHESIS; BROMIDE; DONOR;

D O I：

10.1021/jo500730y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：4676 / 4686

页数：11

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