Hot Topics in Natural Products (Track)


TOTAL SYNTHESIS OF (+)-TRILOBACIN

Te-ik Sohn, Mi Jung Kim and Deukjoon Kim

College of Pharmacy, Seoul National University


Abstract:


Trilobacin, the first known member of adjacent bis-tetrahydrofuran (THF) annonaceous acetogenins with a threo, trans, erythro, cis, threo backbone, was isolated from Asmina triloba by McLaughlin and co-workers in 1992. The impressive potency of the annonaceous acetogenin against human solid-tumor cell lines, coupled with the fascinating structure and limited availability, has attracted considerable attention from the synthetic community. we reported an asymmetric total synthesis of trilobacin featuring a novel organoselenium-mediated oxonium ion formation/SiO2-promoted fragmentation process for the construction of its erythro-bis(2,2')-THF core.

Keywords: Natural product, total synthesis and trilobacin.