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（-）-vescalagin的全合成，C-葡萄糖基鞣花单宁家族的标志性成员

Total Synthesis of (-)-Vescalagin, the Iconic Member of the C-Glucosidic Ellagitannin Family.

作者信息

Larrieu Romain, Cornu Anaëlle, Pouységu Laurent, Deffieux Denis, Quideau Stéphane

机构信息

Univ. Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405, Talence, Cedex, France.

出版信息

Chemistry. 2025 Jun 17;31(34):e202501159. doi: 10.1002/chem.202501159. Epub 2025 May 23.

DOI:10.1002/chem.202501159
PMID:40162586
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12172579/
Abstract

The first total synthesis of the 2,3,5-O-(S,R)-NonaHydroxyTriPhenoylated (NHTP) and 4,6-O-(S)-HexaHydroxy-DiPhenoylated (HHDP) C-glucosidic ellagitannin (-)-vescalagin was accomplished through a bioinspired route involving intramolecular atroposelective cupric-diamine complex-mediated phenolic couplings of gallates to forge its HHDP and NHTP units and a methoxyamine-driven opening of a glucopyranose intermediate followed by a phenolic aldol-type reaction to form its C-arylglucosidic bond. The minor epimer that resulted from this bond-forming event was used to complete also a first total synthesis of the vescalagin epimer, (-)-castalagin.

摘要

通过一条受生物启发的路线首次全合成了2,3,5-O-(S,R)-九羟基三苯甲酰化（NHTP）和4,6-O-(S)-六羟基二苯甲酰化（HHDP）的C-糖苷鞣花单宁（-）-vescalagin，该路线包括分子内阻转选择性铜-二胺络合物介导的没食子酸盐酚偶联以形成其HHDP和NHTP单元，以及甲氧基胺驱动的吡喃葡萄糖中间体开环，随后进行酚醛醇型反应以形成其C-芳基糖苷键。由该成键事件产生的次要差向异构体也用于完成vescalagin差向异构体（-）-castalagin的首次全合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/120f618360b2/CHEM-31-e202501159-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/56706f4c436f/CHEM-31-e202501159-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/a9e48c860b9d/CHEM-31-e202501159-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/120f618360b2/CHEM-31-e202501159-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/56706f4c436f/CHEM-31-e202501159-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/a9e48c860b9d/CHEM-31-e202501159-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a24f/12172579/120f618360b2/CHEM-31-e202501159-g004.jpg

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