Intramolecular Cyclization Strategies for the Synthesis of Carbo-and Heterocyclic Scaffolds

Friday, October 20, 2017

Dr. Matthew Donahue


University of Southern Mississippi

Hand 1144, 3:30 PM

matthew donahue

Abstract: The synthesis of small molecules remains an important and challenging endeavor in science. In this seminar, I will discuss cyclization strategies we have been investigating to construct carbo- and heterocyclic motifs found in complex natural products and biologically active small molecules. The first vignette will explore the use of an intramolecular phenolic allylation to prepare spiro[4.5]decanes relevant to lycopodium alkaloids, and cyclopian and acorane terpenoids. The second research thrust will focus on utilizing aza-Prins cyclizations of iminium ions generated from chiral, non-racemic homoallylic alcohols for the preparation of multisubstituted piperidines, a common scaffold found in FDA approved pharmaceutical drugs. The last endeavor will demonstrate our collaborative effort in biomedical research on the structure-activity relationship of biaryl quinolines as HIV-Integrase inhibitors. The unifying theme of these research programs is to utilize established chemical reactions to create new molecules with chemical space diversity to address unmet medical needs. 


Bio: Matt Donahue was born and raised in Kenosha, WI. He earned his B.S. degree in chemistry from the University of Wisconsin at Parkside then a Ph.D. from The Ohio State University under the Professor David J. Hart. After a postdoc at Vanderbilt University under Professor Jeffrey N. Johnston, he was employed as a radiosynthesis chemist by Wyeth, Boehringer Ingelheim and then Johnson & Johnson. He then transitioned to academic research at the University of Southern Mississippi were his interests lie in the synthesis of complex molecules and the investigation of new reactions. 

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