Dienedioic acid as a useful diene building block via directed Heck-decarboxylate coupling

Abstract

The concise construction of diene scaffolds is quite useful in the synthesis of polyenes. Many diene building blocks have been developed based on Suzuki, Still and Hiyama couplings. Herein, the commercially available and environmentally friendly compound dienedioic acid is used as a diene building block. Broad substrate scope, good functional group tolerance, and late-stage derivatization of complex drug molecules are achieved. Different moieties can be conveniently introduced to both sides. Piperine and the methyl ester of azoxymycin C are each prepared in three steps. Additionally, one product shows promising anticancer activities in leukemia K562 and MV-4-11 cells. Mechanistic studies indicate that the reaction proceeds through a Heck-decarboxylate coupling procedure, and the carboxylic group acts as a directing group to promote the reaction and control regioselectivity. Our research suggests that dienedioic acid can serve as a good alternative for diene preparation via a directed Heckdecarboxylate coupling.

Molecular Coadsorption of p-Hydroxythiophenol on Silver Nanoparticles Boosts the Plasmon-Mediated Decarboxylation Reaction

“…As one of the important organic reactions, − decarboxylation helps to synthesize new compounds containing C–C or C–X (X = N, P, O) bonds via heterocyclic synthesis. − Moreover, the decarboxylation reaction also provides cost-effective raw materials for the synthesis of new carbon skeletons due to the low price, low toxicity, and high stability of the carboxylic acid compounds . As a result, the decarboxylation reaction has been widely used in the fields of drug synthesis, , chemical industry, , and biology. − At present, decarboxylation reactions are mainly catalyzed by toxic and/or expensive organometallic compounds, − and the reactions are usually carried out in an organic base , and at a high temperature. , …”