Synthetic studies toward C-glucosidic ellagitannins: a biomimetic total synthesis of 5-O-desgalloylepipunicacortein A.
Synthetic studies toward C-glucosidic ellagitannins: a biomimetic total synthesis of 5-O-desgalloylepipunicacortein A.
复制标题
C-葡萄糖苷鞣花单宁的合成研究：5-O-去没食子酰皮布尼卡皮质素 A 的仿生全合成。
作者：
Gaëlle Malik;Anna Natangelo;J. Charris;L. Pouységu;S. Manfredini;D. Cavagnat;T. Buffeteau;D. Deffieux;S. Quideau
C-糖苷鞣花单宁是一类具有很强抗氧化活性的多酚类天然产物，其抗肿瘤和抗病毒活性与其与功能蛋白和结构蛋白的相互作用有关。迄今为止，大多数合成鞣花单宁的努力都涉及吡喃葡萄糖类物质。本文描述了获得C-糖苷鞣花单宁的合成策略的开发，所述C-糖苷鞣花单宁的特征性结构特征包括通过C-芳基糖苷键连接至开链葡萄糖核心的阻转异构的六羟基二苯酰基（HHDP）或九羟基三苯酰基（NHTP）单元。通过使用天然鞣花酸双内酯作为所需HHDP单元的前体或通过实施阻转选择性分子内氧化双芳基偶联以形成该HHDP单元，实现了含双芳基HHDP的5-O-去没食子酰哌啶单萜素A（1 β）的全合成。两种途径在该合成的倒数第二步中会聚，以使得能够在标题化合物中仿生形成关键的C-芳基糖苷键。
C-glucosidic ellagitannins constitute a subclass of bioactive polyphenolic natural products with strong antioxidant properties, as well as promising antitumoral and antiviral activities that are related to their capacity to interact with both functional and structural proteins. To date, most synthetic efforts toward ellagitannins have concerned glucopyranosic species. The development of a synthetic strategy to access C-glucosidic ellagitannins, whose characteristic structural feature includes an atropoisomeric hexahydroxydiphenoyl (HHDP) or a nonahydroxyterphenoyl (NHTP) unit that is linked to an open-chain glucose core by a C-aryl glucosidic bond, is described herein. The total synthesis of the biarylic HHDP-containing 5-O-desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis-lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C-aryl glucosidic bond in the title compound.
影响因子：
5.1
作者：
KASHIWADA, Y;NONAKA, G;LEE, KH
通讯作者：
LEE, KH
影响因子：
3.8
作者：
KASHIWADA, Y;NONAKA, G;LEE, KH
通讯作者：
LEE, KH