Stereoselective Synthesis of Spiro Bis-C,C-α-arylglycosides by Tandem Heck Type C-Glycosylation and Friedel-Crafts Cyclization

被引：11

作者：

Chen, Yen-Bo ^{[1
,2
]}

Liu, Shi-Hao ^{[2
]}

Hsieh, Min-Tsang ^{[1
,4
]}

Chang, Chih-Shiang ^{[1
,2
]}

Lin, Chun-Hung ^{[3
]}

Chen, Chen-Yin ^{[1
,2
]}

Chen, Po-Yen ^{[1
,2
]}

Lin, Hui-Chang ^{[1
,2
]}

机构：

[1] China Med Univ, Sch Pharm, 91 Hsueh Shih Rd, Taichung 40402, Taiwan

[2] China Med Univ, Grad Inst Pharmaceut Chem, 91 Hsueh Shih Rd, Taichung 40402, Taiwan

[3] Acad Sinica, Inst Biol Chem, 128,Acad Rd,Sect 2, Taipei 11529, Taiwan

[4] China Med Univ Hosp, Chinese Med Res & Dev Ctr, 2 Yude Rd, Taichung 40447, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期

关键词：

CATALYZED COUPLING REACTION; GLYCOSIDE SYNTHESIS; ARYLBORONIC ACIDS; FACILE SYNTHESIS; ORGANIC HALIDES; EXO-GLYCALS; PALLADIUM; REAGENTS; ANALOGS; POTENT;

D O I：

10.1021/acs.joc.5b02891

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spiro bis-C,C-alpha-arylglycosides were synthesized in three steps in 78-85% overall yields starting from exo-glycals. The initial Heck type C-aryl addition of exo-glycals with arylboronic acids afforded alpha-aryl-beta-substituted C-glycosides with exclusive alpha-stereoselectivity. Among the products, beta-ethanal alpha-aryl C-glycosides further reacted with alkylthiol in the presence of InCl3, followed by in situ Friedel-Crafts cyclization to yield the desirable final products. We proposed a mechanism to explain how the alpha-aryl group serves as a main determinant of the cyclization.

引用

页码：3007 / 3016

页数：10

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