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

Abstract

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