Brian E. Love
Associate Professor, Organic Chemistry
Postdoctoral Fellow, UCLA (1985-1987)
Ph.D., Princeton University (1986)
B.S., Texas Christian University (1980)
Synthetic methods, synthesis of biologically active compounds, synthesis of analytical reagents
Though our research interests span several topics, the theme common to them all is the development of new methodology in organic synthesis (that is, designing new reagents and new synthetic pathways for creating compounds of interest) with an emphasis on practicality. One current area of research is the development of new routes to compounds known as b
-carbolines. Many b
-carbolines possess significant biological activity, and so are of interest to the pharmaceutical industry.We are seeking to develop quick and efficient methods of preparing them from the readily available starting material known as indole.
Another area of interest is the synthesis of quinones and their dimeric analogues known as diquinones, both of which can be made by oxidation of electron-rich aromatic compounds. We are seeking to develop methods to selectively produce either quinones or the corresponding diquinones from the same starting materials. We also are investigating elaboration of such molecules into more highly substituted analogues which may possess biological activity.
Other projects have an analytical "flavor" to them. For example, we are involved in the development of reagents for determining the enantiomeric excess of chiral amines (and also alcohols) via NMR. We are also seeking to develop improved methods of titrating moisture-sensitive reagents (determining their concentrations when in solution).In all cases, we are looking to develop something that is practical and easy to use.
Fall 2014 Research Group
From L to R: Alex Simmons, Dr. Brian Love, Ethan Chiapissi
Selected Publications Related to Projects Described Above
1. Brian E. Love and Prasad S. Raje, "Preparation of 1-Aryl-b-carbolines," Journal of Organic Chemistry, 1994, 59, 3219.
2. Brian E. Love and Prasad S. Raje, "Improved Synthesis of 1-Aryl-b-carbolines," Synlett, 1995, 1061-1062.
3. Brian E. Love, "Synthesis of b-Carbolines. A Review," Organic Preparations and Procedures International, 1996, 28, 1-64.
4. Brian E. Love and Edward G. Jones, "The Use of Salicylaldehyde Phenylhydrazone as an Indicator for the Titration of Organometallic Reagents," Journal of Organic Chemistry, 1999, 64, 3755-56.
5. Brian E. Love, "Synthesis of Carbolines Possessing Antitumor Activity," Topics in Heterocyclic Chemistry, 2006, 93-128.
6. Brian E. Love Jeffrey Bonner-Stewart and Lori A. Forrest, "Improved Synthesis of Diquinones," Synlett, 2009, 813-817.
7. Brian E. Love Jeffrey Bonner-Stewart and Lori A. Forrest, "An Efficient Synthesis of Oosporein," Tetrahedron Lett., 2009, 50, 5050-5052.
8. Brian E. Love, Brian C. Duffy and Alexander L. Simmons, "Effects of Reaction Conditions on Quinone/Diquinone Product Ratios in the Oxidation of 1,4-Dimethoxybenzene Derivatives with Ceric Ammonium Nitrate," Tetrahedron Lett., 2014, 55, 1994-1997.
9. Brian E. Love, "Isolation and synthesis of polyoxygenated dibenzofurans possessing biological activity," Eur J. Med. Chem., 2015, in press.
MS Theses Directed
James Wynne (1996) "New Synthetic Approaches to b-Carbolines"
Darrell Campanella (1997) "New Reagents for Kinetic Resolution of Alcohols"
Shawn Bartley (1997)"The Attempted Synthesis of Benzofuro[2,3-c]pyridines"
Jeff Rorer (1998) "Synthesis of N-Tosyl Imines"
Chip Al-Hashimi (2001) "Potential Pathways to b-Carbolines"
Nicole Morris (2002) "Attempted Syntheses of Chiral Primary Amines and New Reagents for Determining Their Enantiomeric Excess"
Rob Bills (2002) "Synthesis and Enantiomeric Excess Determination of 1,1'-Bi-2-naphthol (BINOL)"
Brian Duffy (2012) "Solvent and Solubility Effects on Quinone Ratios"