Total Synthesis of (−)‐Vescalagin, the Iconic Member of the <i>C</i> ‐Glucosidic Ellagitannin Family
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.
Authors
- Denis Deffieux (ORCID: https://orcid.org/0000-0002-6287-1835)
- Anaëlle Cornu
- Laurent Pouységu (ORCID: https://orcid.org/0000-0002-4310-848X)
- Stéphane Quideau (ORCID: https://orcid.org/0000-0002-7079-9757)
- Romain Larrieu
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université de Bordeaux (FR)
- Institut des Sciences Moléculaires (FR)
- Institut de Mathématiques de Bordeaux (FR)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2025-03-31
- DOI
- https://doi.org/10.1002/chem.202501159
- Citations
- 1
- Primary Topic
- Vanadium and Halogenation Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.54