New Strategies for the Synthesis of Complex, Polycyclic Molecules

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With this award, the Chemical Synthesis program of the Division of Chemistry is supporting the research of Professor Corinna Schindler at the University of Michigan to develop new strategies for the synthesis of naturally occurring molecules that hold great promise due to their biological activity. The selective synthesis of complex, polycyclic structures remains challenging as the majority of currently available methodologies have been developed for simple molecular scaffolds. Consequently, more complex structures often fail to react. The research described seeks to advance sustainable synthetic strategies relying on either the recognition of hidden symmetry elements or visible light photocatalysis to greatly simplify access to these desirable compounds of biological importance. This research focus is an integral component of the principal investigator’s educational plans which include training opportunities for undergraduate and graduate students, both in large introductory science classes and in her research laboratory, as well as outreach programs designed to engage Detroit elementary school girls, middle school students, and the general public to spark and sustain an interest in scientific research. The overarching goal of Professor Schindler’s research program is to address the challenge of selective carbon-carbon bond formation in complex systems. The studies proposed will establish new synthetic approaches to enable direct access to four classes of important complex, polycyclic molecules of biological importance. Specifically, two distinct objectives will be pursued that (i) build on and develop hidden symmetry elements as an enabling design element in complex molecule synthesis and (ii) advance visible light-mediated [2+2]-cycloadditions to rapidly access strained, polycyclic systems incorporating four-membered rings. Together, these new strategies are expected to (iii) enable the synthesis of desirable biologically active complex, polycyclic molecules. The objectives described seek to complement and advance currently existing synthetic methods to enable rapid and efficient access to carbocyclic structures of biological importance.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.