Flexible synthesis of vulpinic acids from tetronic acid

Several vulpinic acids were synthesized in a few steps from a single precursor, the tetronic acid. This commercial compound was converted in a few steps to an iodide. Suzuki-Miyaura cross-couplings involving this common intermediate and various arylboronates allowed to gain access to several vulpinic acids (or methyl pulvinates). Among them, two natural products, vulpinic acid and pinastric acid, were prepared.

Tetronic acid was converted in a few steps to an alkenyl iodide which served as a common precursor for several vulpinic acids (methyl pulvinates), bearing different Ar groups, and obtained via Suzuki-Miyaura cross-couplings.