Studies on natural P-terphenyls: Total syntheses of vialinin A and terrestrin B

Abstract

A powerful inhibitor of TNF-α production, vialinin A, was synthesized from sesamol through a series of reactions involving double Suzuki-Miyaura coupling, 2,3-dichloro-5,6-dicyano-l,4-benzoquino (DDQ) mediated de-methoxymethylation and oxidative removal of meth-ylene acetal by lead tetraacetate. The synthetic method also made it possible to prepare a related compound, terrestrin B.