Towards the Synthesis, Biological Studies, and Cellular Target Identification of Rubesanolides A and B




Rerick, Allison

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This work explores the effort towards a total synthesis of rubesanolides A and B, diterpenoids containing fused b-lactones. These natural products, fully characterized in 2011 by Zou and coworkers, originate from Isodon rubescens, a family of flowering plants native to China. It is believed that the rubesanolides may possess anticancer, antibacterial, or antibiofilm properties, but they have not been extensively studied. To this end, we have developed a synthetic strategy to these natural products using the concept of pharmacophore-directed retrosynthesis (PDR). We also aimed to incorporate organocascade reactions developed in the Romo lab into the total synthesis. We describe initial biological studies of congeners; proteomic studies of derivatives and, ultimately, probes inspired by the natural products themselves will allow for elucidation of the natural products’ biological activity and establish a structure-activity-relationship (SAR) of the rubesanolides.