With this CAREER Award, the Chemical Synthesis Program of the Division of Chemistry is supporting the research of Professor Thomas Maimone of the University of California, Berkeley. Professor Maimone is developing new tools for organic synthesis that are designed to facilitate the construction of complex polycyclic compounds. One tool allows new rings to be added to a molecular structure, and another allows the size of the ring to be changed by an oxidation reaction. Professor Maimone is applying these synthetic tools to develop rapid and efficient syntheses of molecular structures in a family of natural product called polycyclic polyprenylated acylphloroglucinols. Members of this family of are protect neurons and have potential use for the treatment of neurodegenerative conditions such as Alzheimer's disease. This work is expected to have broad applications in the field of organic synthesis as well as medicinal chemistry. As the educational component of his project, Professor Maimone is developing a research symposium that focuses on introducing community college students to synthetic organic chemistry research. A hands-on research component has been designed for intensive summer research under the mentorship of a UC-Berkeley graduate chemistry student. In addition to activities at the community college level, this CAREER Award also supports research activities at the elementary school level as part of the Bay Area Scientists in Schools(BASIS) program in the Berkeley and Oakland unified school districts. Both of these endeavors are expected to increase interest in science fields, particularly chemistry, across a highly diverse student body representative of the larger Bay Area community.
Professor Maimone is developing new synthetic reactions to facilitate the construction of complex polycyclic compounds. The simple feedstock chemical diketene is being developed as a novel annulation reagent. In addition, this research describes the study of oxidative carbon-carbon bond rearrangements promoted by hypervalent iodine complexes. These two steps work together to produce the conserved bicyclo [3.3.1] nonane trione motif of the polycyclic polyprenylated acylphloroglucinols. Members of this family show a variety of biological activities, including inhibition of neurotransmitter reuptake (hyperforin) and choline acetyltransferase enhancement (garsubellin A). The new synthetic methods and access to this family of natural products may have applications in the fields of organic synthesis and medicinal chemistry. The educational plan includes the development of new course material on the synthesis of heterocycles, which is targeted towards advanced undergraduate chemistry majors and graduate students. Many chemists work in the pharmaceutical industry where such knowledge of heterocyclic chemistry is important.
