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CHEMISTRY & BIOCHEMISTRY

Carl J. Lovely

Carl J. Lovely

Professor and Distinguished Teaching Professor
Associate Department Chair


Office: 204 Chemistry Research Building (CRB)
Email: lovely@uta.edu
Phone: 817-272-5446
Mentis Profile

Education:
B.Sc.
 University of Birmingham, 1987
Ph.D. University of Birmingham, 1990
Post Doctorate:
Universität Heidelberg, 1991
The Ohio State University, 1992-1996


Research Interests

Heterocyclic Chemistry: A long standing research program in the Lovely group centers on the development of new methods for the construction and elaboration of heterocyclic molecules. Recent efforts in our lab have focused on the development of efficient synthetic approaches to imidazole-containing natural products, particularly those in the oroidin and Leucetta families of marine alkaloids. Recently completed targets include cyclooroidin (1), the reported structure of nagelamide D (2), calcaridine A (3) and kealiiquinone (4). We have developed strategies which rely on the elaboration of intact imidazoles through position-specific functionalization and subsequent manipulation.

Figure 1.

 heterocyclic molecules

Current efforts are focused on the total synthesis of more complex members of both families of alkaloids, in particular several derivatives in the nagelamide family including nagelamide A (5) and C (6), which we hope themselves will in turn serve as precursors of other derivatives. Ceratinadin (7), a heterocycle rich spiro isoxazoline is under study in our lab – its total synthesis is providing the platform for the development of several new synthetic methods. Other targets of interest include the Leucetta-derived alkaloids spirocalcaridine A (8) and spiroleucettadine (9).

Figure. 2

 Nagelamide molecules

Lovely

While our programs are largely centered on the total synthesis of marine-derived alkaloids, nearly all of the syntheses require the development of new synthetic methodology, thus providing training in both target-directed synthesis and methodology. In addition, when the opportunity presents itself we explore the biological utility of both the synthetic natural product and intermediates through collaborations.


Carl is a native of the UK and grew up in the small brewery town of Burton-on-Trent, in central England. He attended The University of Birmingham where he obtained a B.Sc. (Hons) in Chemistry in 1987 and remained there to conduct Ph.D. studies with Professor W. Brian Jennings on oxaziridine chemistry (1990). After a postdoctoral stay, supported by a Royal Society Fellowship at the Organisches-Chemisches Institut der Universität Heidelberg with Prof. Klaus Weinges (1991), he then moved to the US, where he did postdoctoral work first with Prof. Leo Paquette (1992-93, Department of Chemistry) and then Prof. Robert Brueggemeier (1993-96, College of Pharmacy), both at The Ohio State University. He moved to the University of Texas at Arlington (UTA) as an assistant professor in 1996 and was subsequently promoted to associate professor in 2002, and full professor in 2008. In 2010 he was inducted into the Academy of Distinguished Teachers at UTA, becoming a Distinguished Teaching Professor. His research interests include the development of synthetic methods for heterocycle synthesis, mostly focused on imidazole chemistry. A second area of activity revolves around the discovery and development of transition metalmediated and -catalyzed reactions. The overarching goal of this methods development is the application of these new reactions to natural products total synthesis.


 

  1. “Total Synthesis of 7’-Desmethylkealiiquinone, 4’-Desmethoxykealiiquinone and 2-Deoxykealiiquinone” Lima, H.M.; Rasapalli, S.; Yousufuddin, M.; Lovely, C.J. J. Org. Chem. 2014, 79, 2481.

 

  1. “Studies towards the Leucetta-derived Alkaloids Spirocalcaridine A and B – Possible Biosynthetic Implications” Koswatta, P.B.: Das, J.; Yousufuddin, M.; Lovely, C.J.  Eur. J. Org. Chem. 2015, 2603-2013.

 

  1. “Preparation and Diels-Alder Reactions of 1’-Heterosubstituted Vinylimidazoles” Ray, A.; Mukherjee, S.; Das, J.; Bhandari, M.K.; Du, H.; Yousufuddin, M.; Lovely, C.J. Tetrahedron Lett2015, 56, 3518-3522. (Invited contribution for Harry Wassermann special issue)

 

  1. “Dearomatizing Spirocyclization Reactions of Propargyl Cyanamides” Singh, R.P.; Spears, J.A.; Dalipe, A.; Yousufuddin, M.; Lovely, C.J. Tetrahedron Lett. 2016, 57, 3096-3099.

 

  1. “An Asymmetric Total Synthesis of Martinellic Acid” Badarinarayana, V.; Mahmud, H.; Lovely, C.J. Heterocycles 2017, 95, 1082-1105. (Invited contribution for Masakatsu Shibasaki Special Issue).

 

  1. “Tandem Oxidative Dearomatizing Spirocyclizations of Propargylic Guanidines and Ureas” Singh, R.P.; Das, J.K, Yousufuddin, M.; Gout, D.; Lovely, C.J. Org. Lett. 2017, 19, 4110-4113.

 

  1. “Thio Acid-Mediated Conversion of Azides to Amides – Exploratory Studies En Route to Oroidin Alkaloids” Herath, A.K.; Bhandari, M.R.; Gout, D.; Yousufuddin, M.; Lovely, C.J. Tetrahedron Lett. 2017, 58, 3913-3918.

 

  1. “Steric Buttressing in the Pauson-Khand Reactions of Benzyl Enynes” Madu, C.E.; Dias, H.V.R.; Lovely, C.J. Tetrahedron 2017, 73, 6118-6137.

 

  1. “[3-(4-Methoxyphenyl)-1-[(4-methoxyphenyl)methyl]prop-2-ynyl]-methylcyanamide” Yousufuddin, M.; Morales, R.; Cassis, W.; Brown, G. W.; Singh, R.P.; Lovely, C.J. IUCrDat 2018, 3, x180389.

 

  1. “Intramolecular Diels-Reaction of a Silyl-substituted Vinylimidazole – en route to the Fully Substituted Cyclopentane Core of Oroidin Dimers” Ray, A.; Yousufuddin, M.; Gout, D.; Lovely, C.J. Org. Lett. 2018, 20, 5964–5968.

 

  1. “Heterosubstituted 4-Vinylimidazoles – Preparation and Diels-Alder Reactions” Ray, A.; Yousufuddin, M., Gout, D.; Lovely, C.J. Heterocycles 2019, 99, in press (Invited contribution for Professor Tohru Fukuyama Special Issue).

Book chapter

  1. “Isolation, Biosynthesis and Synthesis of the Nagelamides” Das, J.; Bhandari, M.; Lovely, C.J. Studies in Natural Products Chemistry Vol 50, Chapter 10, pp 341-371, edited by Att-ur-Rahman, Elsevier, Amsterdam (2016).

 


College of Science Outstanding Research Award 2012


Academy of Distinguished Teachers, UTA, 2010


College of Science Outstanding Teacher, 2007


Royal Society European Exchange Postdoctoral Fellowship, 1991