Asymmetric Total Synthesis of Trilobacin via Organoselenium-Mediated Oxonium Ion Formation/SiO2-Promoted Fragmentation

An asymmetric total synthesis of trilobacin (1), an annonaceous acetogenin with potent anticancer activities, was accomplished wherein the construction of its etythro-bis(2,2')-tetrahydrofuran core 2 featured a novel organoselenium-mediated oxonium ion formation/SiO2-promoted fragmentation of alpha,alpha'-cis-oxocene 3.