Innovative Approaches to Macrocyclic Natural Products

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The Chemical Synthesis Program of the Chemistry Division supports this project by Professor Rich G. Carter. Professor Carter and his co-investigator, Professor Cheong, are both a faculty members in the Department of Chemistry at Oregon State University. His group is exploring the chemistry of an exciting new series of polyketide natural products called the mandelalides and madeirolides. The overarching goal of this proposal is to develop innovative methods for the construction of these natural products, which advance the field in both reaction and strategy development. These compounds have shown promising cytotoxic and antifungal activities. The project brings together expertise in both experimental (Professor Carter) and computational (Professor Cheung) organic chemistry. Professor Carter's group is well positioned to provide the highest level of education and training for students underrepresented in science. Professional development efforts for students participating in this project are integrated into the program. In addition, outreach activities to engage the broader community on the importance of chemistry are planned. The total synthesis of complex natural products has proven to be an important test bed for the development of new synthetic strategy as well as for the validation of novel chemical methodologies. The proposed syntheses of mandelalides A-B and madeirolide A push the limits of modern organic synthesis. One new methods is the development of a reliable asymmetric dihydroxylation of cis-alkenes to rapidly access trans diols, which is integral to these projects. In addition, the proposed syntheses showcase silver-catalyzed cyclizations of propargylic benzoates. The educational plan includes professional development training for graduate students through an NSF Graduate Research Trainingship Innovation in Graduate Education (NRT IGE) grant at Oregon State University and community engagement through outreach activities at one or two additional schools within the State of Oregon.