TOWARD THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF ALOPECURONE C
Noah Burlow, Kellan Lamb, Jared Shaw.
University of California, Davis, Davis, CA.
Progress toward the first total synthesis of alopecurone C, a resveratrol-derived flavanostilbene natural product, is described. Our interest in this molecule stems from its reported antibiotic activity which includes the inhibition of greater than 20 strains of methicillin-resistant Staphylococcus aureus (MRSA). To date, we have assembled the dihydrobenzofuran core using Rh-catalyzed asymmetric C-H insertion methodology previously developed in our lab. This single transformation established 2 of the 3 stereogenic centers present in the molecule. Current synthetic efforts are focused on the flavanone fragment, which we aim to construct by organocatalytic cyclization of an ortho-hydroxychalcone intermediate.