Synthesis of 3-phenyldibenzo[b,d]furan-type bioprobes utilizing vialinin B as a structural motif

Abstract

ABSTRACTVialinin B is a natural 3-phenyldibenzo[b,d]furan product with a powerful inhibitory activity against tumor necrosis factor (TNF)–α production. This article describes the synthesis of three types of biotinylated p-terphenyls designed for clarifying the target molecule of vialinin B. Construction of the carbon backbone of the core was accomplished by stepwise Suzuki–Miyaura coupling while the phenyl dibenzofuran moiety was built up by the Ullmann reaction. The biotinyl unit was attached through click chemistry.