Synthesis of aryl enopyranones directly from glycals and aromatic halides to access 2-deoxy-β-C-aryl glycosides

被引:1
作者
Zargar, Irshad Ahmad [1 ,2 ]
Rasool, Bisma [1 ,2 ]
Bappa, S. K. [3 ]
Mukherjee, Debaraj [2 ,3 ]
机构
[1] CSIR Indian Inst Integrat Med IIIM, Nat Prod & Med Chem Div, Jammu 180001, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] Bose Inst Kolkata, Dept Chem Sci, EN 80,Sect 5, Kolkata 700091, WB, India
关键词
CROSS-COUPLING REACTIONS; C-H FUNCTIONALIZATION; HECK REACTION; LIGAND; GLYCOSYLATION; DERIVATIVES; DISCOVERY; ARENES;
D O I
10.1039/d4ob01172d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of aryl enopyranones via an oxidative Heck-type coupling reaction between ether protected d/l-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact via the Saegusa-Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-beta-aryl-C-glycosides after Pd/C reduction. An efficient synthesis of aryl enopyranones via an oxidative Heck-type coupling reaction between ether protected d/l-glycals and different aryl halides is developed. The synthesized aryl enopyranones were further transformed into medicinally important 2-deoxy-beta-aryl-C-glycosides.
引用
收藏
页码:6941 / 6945
页数:5
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