Verification of Biaryl-Structure Axial Chirality Produced in Ellagitannins by Chemical Oxidation,Organic Letters

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Verification of Biaryl-Structure Axial Chirality Produced in Ellagitannins by Chemical Oxidation
Organic Letters ( IF 4.9 ) Pub Date : 2022-11-03 , DOI: 10.1021/acs.orglett.2c03173
Shinnosuke Wakamori ₁ , Rumi Osada ₁ , Shintaro Matsumoto ₁ , Reina Kusuki ₁ , Kei Murakami ₁

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The axial chirality of hexahydroxydiphenoyl (HHDP) groups contained in ellagitannins depends on the bridging position of d-glucose. The 4,6-O-HHDP group predominantly exhibits S-type chirality. This study elucidated the formation of the 4,6-O-(R)-HHDP group and subsequent axial isomerization by means of oxidative coupling of galloyl groups, which resulted in S chirality.

中文翻译：

通过化学氧化验证鞣花单宁中产生的双芳基结构轴向手性

鞣花单宁中所含的六羟基联苯酰 (HHDP) 基团的轴向手性取决于d -葡萄糖的桥接位置。4,6- O -HHDP 基团主要表现出S型手性。本研究阐明了 4,6- O -( R )-HHDP 基团的形成以及随后通过没食子酰基的氧化偶联产生的轴向异构化，从而导致S手性。

更新日期：2022-11-03

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