The University of Texas at Arlington

Carl J. Lovely

Carl J. Lovely

Professor and Distinguished Teaching Professor

Office: CRB 204, Email: lovely@uta.edu, Phone: 817-272-5446, FAX: 817-272-3808

Research GroupResearch ProfileCourses

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).

Fig. 2

Nagelamide molecules

 

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.

 


Dias, H. V. R.; Lovely, C. J.  Carbonyl and Ethylene Adducts of Coinage Metals Supported by Tris(pyrazolyl)borate Ligands and Silver Mediated Atom Transfer Reactions, Chem. Rev. 2008, 108, 3223.

Lovely, C. J.; Badarinarayana, V.  Synthetic Studies towards the Martinella Alkaloids, Curr. Org. Chem., 2008, 12, 1431.

Koswatta, P. B.; Sivappa, R.; Dias, H. V. R.; Lovely, C. J.  Total Synthesis of (±)-Calcaridine A and (±)-epi-Calcaridine A, Org. Lett., 2008, 10, 5055.

Lovely, C. J.; Flores, J. A.; Meng, X.; Dias, H. V. R.  Silver-Catalyzed C-H Insertion Reactions with Donor-Acceptor Diazoacetates,  Synlett 2009, 129.

Bhandari, M. R.; Sivappa, R.; Lovely, C. J.  Total Synthesis of the Putative Structure of Nagelamide D, 
Org. Lett.
2009, 11, 1535.

Koswatta, P.; Lovely, C. J.  Total Synthesis of Preclathridine A and Clathridine A, Tetrahedron Lett.  2009, 50, 4998.   

Sivappa, R.; Mukherjee, S.; Lovely, C. J.  Studies Toward the Total Synthesis of Oroidin Dimers, Org. Biomol. Chem. 2009, 7, 3215. 

 Flores, J. A.; Badarinarayana, V.; Singh, S.; Lovely, C. J.; Dias, H. V. R.  Synthesis and Catalytic Activity of an Electron-Deficient Copper-Ethylene Triazapentadienyl Complex, Dalton Trans. 2009. 7648.

Koswatta, P. B.; Sivappa, R.; Dias, H. V. R.; Lovely, C. J.  Total Synthesis of the Leucetta-Derived Alkaloid Calcaridine A, Synthesis 2009, 2970.

Panduka, P. B.; Lovely, C. J.  Total Synthesis of Naamidine G and 14-methoxynaamidine G, Tetrahedron Lett. 2010, 51, 164.

Mukherjee, S.; Sivappa, R; Yousufuddin, M.; Lovely, C.J.  An Approach to the Oxazoline Fragment of Nagelamide R, Synlett 2010, 817.

Lovely, C. J., Sivappa, R.; Mukherjee, S.; Doundoulakis, T.; Lima, H. M.; Yousufuddin, M.  Efficient Preparation of Urocanic Acid Derivatives from Histidine, Heterocycles 2010, 80, 1353.

Koswatta, P. B.; Lovely, C. J.  Concise Total Synthesis of Naamine G and Naamidine H, Chem. Commun. 2010, 2148.

Mukherjee, S.; Sivappa, R.; Yousufuddin, M.; Lovely, C.J. "The Total Synthesis of ent-Cyclooroidin” Org. Lett. 2010, 12, 4940.

Breitbach, Z.S.; Feng, Q.; Koswatta, P.B.; Dodbiba, E. Lovely C. J.; Armstrong, D.W. "The Enantiomeric Separation of 4,5-Disubstituted Imidazoles by HPLC and CE using Cyclodextrin-Based Chiral Selectors” Supramol. Chem. 2010, 22, 758.

Koswatta, P.B.; Lovely, C.J. "Structure and Synthesis of 2-Aminoimidazole Alkaloids from Leucetta and Clathrina Sponges” Nat. Prod. Rep. 2011, 28, 511.

Bhandari, M.R.; Yousufuddin, M.; Lovely, C.J. "A Diversity-Oriented Approach to Pyrrole-Imidazole Alkaloid Frameworks” Org. Lett. 2011, 13, 1382.

Intramolecular Diels-Alder Reactions of 4-Vinylimidazoles” He, Y.; Krishnamoorthy, P.; Lima, H.; Chen, Y.; Wu, H.; Sivappa, R.; Dias, H.V.R.; Lovely, C.J. Org. Biomol. Chem. 2011, 9, 2685.

Lima, H.M.; Garcia-Barboza, B.J.; Khatibi, N.N.; Lovely, C.J.Total syntheses of Isonaamine C and Isonaamidine E” Tetrahedron Lett. 2011, 52, 5725.

Lima, H.M.; Lovely, C.J., "Synthesis of 2-Imidazolones and 2-Iminoimidazoles” Org. Lett. 2011, 13, 5736.

"Total Synthesis of 7’-Desmethylkealiiquinone” Lima, H.M.; Sivappa, R.; Yousufuddin, M.; Lovely, C.J. Org. Lett. 2012, 14, 2274.

“The Enantiomeric Separation of Tetrahydrobenzimidazole Intermediates by HPLC and CE Using Cyclodextrin and Cyclofructan Based Chiral Selectors” Perera, S.; Na, Y.-C.; Doundoulakis, T.; Ngo, V.J.; Feng, Q.; Breitbach, Z.S.; Lovely, C.J.; Armstrong, D.W. Chirality 2012 25, 133.

“Total Syntheses of Kealiinines A-C” Das, J.; Koswatta, P.B.; Jones, J.D.; Yousufuddin, M.; Lovely, C.J. Org. Lett. 2012, 14, 6210

“Total Syntheses of Oroidin, Hymenidin and Clathrodin”, Sivappa, R.; Kumbam, V.; Dhawane, A.; Golen, J.A.; Lovely, C.J.; Rheingold, A.L. Org. Biomol. Chem. 2013, 11, 4133.

“Total Syntheses and Cytotoxicity of Kealiiquinone, 2-Deoxykealiiquinone and Analogs” Das, J.; Bhan, A.; Mandal, S.S.; Lovely, C.J. Bioorg. Med. Chem. Lett. 2013, accepted for publication.

B.Sc., University of Birmingham (1987)

Ph.D., University of Birmingham (1990)

Postdoctoral Researcher:
Universität Heidelberg (1991),
The Ohio State University (1992-1996)

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.

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

Department of Chemistry and Biochemistry

The University of Texas at Arlington · Arlington, Texas 76019-0065 USA

Phone: 817-272-3171 | Fax: 817-272-3808

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