Advancing Synthetic Methodology through Total Synthesis of Complex Molecules

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ABSTRACTIn this project funded by the Chemical Synthesis program of the Chemistry Division of the National Science Foundation, Professor Armen Zakarian of the University of California, Santa Barbara, is developing new methods and synthetic strategies for the preparation of a broad range of organic materials with useful properties. These methods are designed to make the synthesis of such materials from readily available sources shorter, and therefore more economical, energy-efficient, and less wasteful. The types of compounds that can be prepared using the new chemical tools find application primarily in pharmaceutical research and industry, and secondarily in materials and agricultural sciences.The goals of this research project are two-fold. The first major goal is the development of modern C-H functionalization methods for the synthesis of benzofurans and benzofuran-containing natural products of biomedical significance, such as galanthamine. A copper-catalyzed direct aryl C-H functionalization method has been identified as highly promising to provide a path to functionalized benzofurans under mild conditions. Studies of its scope and application in the concise synthesis of galanthamine are being currently pursued. The second goal is the development of lanthanide catalysis for activation of dienes in the Diels Alder reaction. This approach features in the total synthesis of muironolide A, an exceedingly rare marine natural product with promising but unexplored biomedical potential. An outreach program is being developed between graduate students in the Zakarian group and area elementary school students and teachers involved in the SciTrak program hosted at UC Santa Barbara.