Jeremy B. Morgan
Aziridine Synthesis and Ring Opening
The cost-effective synthesis of nitrogen-containing small molecules remains an important challenge in organic chemistry. The importance of carbon-nitrogen bonds can be highlighted by simply observing their prevalence in commercial pharmaceuticals, where 80-90% of the top 200 medications contain at least on carbon-nitrogen bond. Aziridines, three-membered nitrogen-containing rings, are valuable intermediates for the synthesis of small molecules. The Morgan group has become interested in developing new methodologies for accessing enantioenriched aziridines. Once in hand, the activated aziridines are subjected to stereospecific ring opening reactions by control of both regio and enantiospecificity. Direct access to enantioenriched tryptamine, phenethylamine, diamine, amino alcohol, and amino halogen derivatives is possible from a common aziridine precursor.
Cinchona Alkaloid Derivatives for the Treatment of Malaria
Malaria claims more than 800,000 lives each year, primarily outside the US. The classic approach to treating malaria relied on the Cinchona alkaloids, typically quinine. Since the early 1900s, new approaches to combating malaria, including chloroquine, mefloquine, were inspired by the Cinchona alkaloid structure; however, resistance to these drugs has been building over the past decades. The Morgan group was inspired by the low occurrence of quinine resistance to investigate new modifications of the Cinchona core.
Through a collaboration with the Roepe group at Georgetown University, we have begun testing new Cinchona alkaloid derivatives against quinine-sensitive and quinine-resistant Plasmodium falciparum strains. Our initial approach employed direct, one-step variation of the alkene of quinine utilizing a Heck reaction. Though improvement in vitro activity was minimal, alkene functionalization led to variation in IC50 values. Alternative structural modifications are currently being pursued.
Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines. Jennifer Cockrell, Christopher Wilhelmsen, Heather Rubin, Allen Martin, and Jeremy B. Morgan. Angew. Chem., Int. Ed. 2012, 51, 9842-9845. [DOI: 10.1002/anie.201204224]
Investigating the Activity of Quinine Analogues versus Chloroquine Resistant Plasmodium falciparum. Theresa Dinio, Alexander P. Gorka, Andrew McGinniss, Paul D. Roepe, and Jeremy B. Morgan. Bioorg. Med. Chem. 2012, 20, 3292-3297. [DOI: 10.1016/j.bmc.2012.03.042]
Phosphine-Catalyzed Heine Reaction. Allen Martin, Kathleen Casto, William Morris, and Jeremy B. Morgan. Org. Lett. 2011, 13, 5444-5447. [DOI: 10.1021/ol202410v]Iodoetherification of Unactivated Alkenes Catalyzed by Diphosphine Palladium(II) Complexes. Todd A. Doroski, Matthew R. Cox, and Jeremy B. Morgan. Tetrahedron Lett. 2009, 50, 5162-5164. [DOI: 10.1016/j.tetlet.2009.06.121]
Occurrence of the Artificial Sweetener Sucralose in Coastal and Marine Waters of the United States. Ralph N. Mead, Jeremy B. Morgan, G. Brooks Avery Jr., Robert J. Kieber, Aleksandra M. Kirk, Stephan A. Skrabal, and Joan D. Willey. Marine Chem. 2009, 166, 13-17. [DOI: 10.1016/j.marchem.2009.09.005]
Publications prior to independent career
Stereocontrolled Synthesis of Functionalized cis-Cyclopentapyrazolidines by 1,3-Dipolar Cycloaddition Reactions of Azomethine Imines. Joshua Gergely, Jeremy B. Morgan, and Larry E. Overman. J. Org. Chem. 2006, 71, 9144-9152. [DOI: 10.1021/jo061537j]
Rh-Catalyzed Enantioselective Diboration of Simple Alkenes: Reaction Development and Substrate Scope. Stephane Trudeau, Jeremy B. Morgan, Mohanish Shrestha, and James P. Morken. J. Org. Chem. 2005, 70, 9538-9544. [DOI: 10.1021/jo051651m]
Catalytic Enantioselective Hydrogenation of Vinyl Bis(boronates). Jeremy B. Morgan and James P. Morken. J. Am. Chem. Soc. 2004, 126, 15338-15339. [DOI: 10.1021/ja044396g]
Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction. Steven P. Miller, Jeremy B. Morgan, Felix J. Nepveux V, and James P. Morken. Org. Lett. 2004, 6, 131-133. [DOI: 10.1021/ol036219a]
Rhodium-Catalyzed Enantioselective Diboration of Simple Alkenes. Jeremy B. Morgan, Steven P. Miller, and James P. Morken. J. Am. Chem. Soc. 2003, 125, 8702-8703. [DOI: 10.1021/ja035851w]
Platinum-Catalyzed Tandem Diboration/Asymmetric Allylboration: Access to Nonracemic Functionalized 1,3-Diols. Jeremy B. Morgan and James P. Morken. Org. Lett. 2003, 5, 2573-2575. [DOI: 10.1021/ol034936z]
Restraint Stress and Corticotropin Releasing Hormone Modulation of Murine Cutaneous POMC mRNA. Melanie S. Flint, Jeremy B. Morgan, Stacey N. Shreve, and Sally S. Tinkle. Stress 2003, 6, 59-62. [DOI: 10.1080/1025389031000088426]