Strategy Driven Synthesis of Complex Alkaloids

With the support of the Chemical Synthesis program in the Division of Chemistry, Professor Thomas Maimone of the University of California, Berkeley will study new synthetic strategies for the construction of complex, nitrogen-containing molecules. At the core of this work is the identification of powerfully simplifying transformations that can lead to the production of topologically unique target molecules with high overall efficiency. The targets chosen for this program challenge the current state-of-the-art in complex molecule synthesis. Results of these endeavors are expected to have a positive impact across the societally important field of organic chemical synthesis which is used to produce medicines, agrochemicals, and materials industrially. This work will also serve as intellectually stimulating training for graduate students who will become future scientists in these fields. Moreover, this grant enables wide-reaching science-focused outreach for Bay Area elementary school students as well as local community college transfer students. Professor Maimone is studying complex alkaloid syntheses of members of the caulamidine and myrmicarin families which have important biological properties and unusual molecular architectures. These biosynthetically mysterious molecules have proven challenging as targets for organic chemical synthesis for many years. Professor Maimone’s work will generate new strategies to construct challenging C–C bond linkages and halogenated Sp3 stereocenters and will also put forth new methods for ring formation using small annulation reagents. This work will not only advance the science of synthesis but allow for the construction of ample quantities of rare natural products for further scientific study. As a part of this project, Professor Maimone is also training his coworkers and preparing them for careers in chemical industries and academia. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.