Scripps Research Institute
Scalable routes to complex terpenes
Dr. Phil S. Baran, a Professor at The Scripps Research Institute received the 2013 MacArthur Fellowships award. Dr. Baran is currently a TEVA Pharmaceuticals Scholars grant holder, awarded in the 2012 competition. His TEVA research project is “Scalable Routes to Complex Terpenes.” Additional information on his research can be found at his website.
The Baran laboratory has been interested in a “two-phase” strategy toward the synthesis of complex terpene natural products such as eudesmanes, taxanes and ingenanes. We wish to further explore and expand the potential scope of this strategy by: 1) developing an efficient and scalable “cyclase phase” to the ent-kaurane and ent-atisane families of natural products; 2) testing the efficiency and selectivity of the ensuing “oxidase phase” in order to target various oxidation levels in the bioactive ent-kaurane family of natural products; and 3) using a semi-synthetic approach as an expedient cyclase phase equivalent and executing a “redox-relay strategy” in the oxidase phase toward a scalable synthesis of ouabain, a cardiotonic steroid. These natural product families offer an ideal opportunity to put into practice the two-phase paradigm and to explore the uncharted realm of chemoselective oxidations during the oxidase phase.
Other than allowing to procure chemicals and pay student stipends, the TEVA grant has allowed for the creation of an educational platform through organic synthesis and has generated a desire to continue pushing the boundaries of chemical feasibility.