Towards a Total Synthesis of Beilschmiedic Acid C
Authors:Katerina Hilleke, Wai Man Yu
Mentor:David Vosburg, Associate Professor of Chemistry, Harvey Mudd College
Beilschmiedic acid C has been isolated from a plant, but has never been prepared in a laboratory before. It has antibiotic activity comparable to that of ampicillin, a commercially used drug. Indeed, several related molecules have demonstrated a wide range of bioactivities, indicating that beilschmiedic acid C might still possess undiscovered medicinal uses. The proposed synthetic strategy follows an electrocyclization cascade and relies heavily on self-assembly, that is, forming molecules which will readily rearrange to produce more complex structures. If successful, our strategy could be applied to the production of various other related bioactive molecules, inclulding endiandramide A and erythrophloin C. Our goal is to synthesize beilschmiedic acid C, to study the electrocyclization cascade, and to determine the relationship between the structures of related molecules and their antibiotic activities. We proceeded through the electrocyclization cascade and deprotection step. We are now poised to generate the full tetracyclic core of beilschmiedic acid C.