Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers. (26th November 2018)

• Record Type: Journal Article
• Authors: Romero, Kevin J.; Galliher, Matthew S.; Raycroft, Mark A. R.; Chauvin, Jean‐Philippe R.; Bosque, Irene; Pratt, Derek A.; Stephenson, Corey R. J.
• Is Part Of: Angewandte Chemie. Volume 130:Number 52(2018)
• Page Start: 17371
• Page End: 17375
• Publication Date: 2018-11-26
• Subjects: Antioxidantien -- Chinonmethide -- Elektrochemie -- Phenylpropenoide -- Resveratrol; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201810870
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p ‐unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical‐trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H‐atom for transfer to the peroxyl radicals that propagate autoxidation. Abstract : Chinonmethid‐Dimere wurden durch milde anodische Oxidation vermittelt durch eine preiswerte und leicht verfügbare Aminbase mit exzellenter Ausbeute und Regiokontrolle hergestellt. Diese Strategie ermöglicht raschen Zugang zu Zwischenprodukten für die katalytische Synthese von Phenylpropenoid‐Oligomeren und bietet ein neues Werkzeug für die Totalsynthese dieser komplexen Moleküle.