Oxidative Coupling of Carboxylic Acid Dianions: The Total Synthesis of (+/-)-Hinokinin and (+/-)-Fomentaric Acid

Article abstract of DOI:10.1021/jo00388a036

The oxidative coupling of carboxylic acid dianion derivatives provides the key intermediates needed for efficient syntheses of the symmetrical lignan hinokinin (9) and the unsymmetrical fungal metabolite fomentaric acid (22).Racemic hinokinin (9), a targed chosen to test the facility of dianion oxidative coupling in the presence of electron-rich aromatic rings, is prepared in an overall conversion of 61 percent from 3,4-(methylenedioxy)hydrocynnamic acid.Racemic fomentaric acid (22), a trisubstituted succinic acid derivative, results from a straightforward two-stepsequence that proceeds in an overall yield of 40 percent from eicosanoic acid.Preliminary studies demonstrate the utility of oxidative coupling in the synthesis of novel surfactant prototypes.