Reagent-controlled stereoselective synthesis of (卤)-gallo- and (卤)-epigallo-catechin gallates

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• 作者：Hiroshi Tanaka ; ^{thiroshi@apc.titech.ac.jp} ; Ayaka Chino ; Takashi Takahashi ; ^{ttak@apc.titech.ac.jp}
• 关键词：Flavonols ; Epoxide ; Enone ; Sulfoxide ; Trifluoroacetic acid
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：16 May, 2012
• 卷：53
• 期：20
• 页码：2493-2495
• 文件大小：289 K

摘要

Synthesis of (卤)-gallocatechin and (卤)-epigallocatechin gallates by electrophilic cycloarylation is reported. The precursors for cyclization were prepared by reagent-controlled stereo-selective opening of epoxide with phenol. Activation of the S-oxidized S,O-acetal enabled electrophilic cycloarylation to stereoselectively provide the acylated catechins.