Michael P. Jennings Associate Professor and Director of Undergraduate Studies SYNTHETIC ORGANIC CHEMISTRY Total synthesis of biologically active natural products, Enantioselective methodology development based on novel chiral ligands, Asymmetric catalysis BS, 1997, University of Illinois; Ph.D., 2001, Purdue University; Postdoctoral Associate, 2001-2003, Scripps Research Institute office: 2076 Shelby Hall Telephone: (205) 348-0351 FAX: (205) 348-9104

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Research Interests

The foremost focus of our research is the synthesis of complex, biologically active natural products. Considerable emphasis will also be placed on the discovery and development of new reactions and synthetic methods for achieving high levels of enantioselective control.

For example, many useful carbon-carbon bond-forming reactions exist; however, conditions for the corresponding asymmetric variants are often under-developed or unexplored. At the core of this research program is the enantioselective development of the [2,3]-Wittig rearrangement and asymmetric alkylation of acyclic carbonyl compounds utilizing novel chiral amine-based ligands derived from a sulfamidate template. With respect to natural products, current targets of interest include Lasonolide A, Didemnaketal A, Caylobolide A, and Miyakolide.

The importance of total synthesis of biologically active natural products and methodology development provides an excellent educational opportunity to all post-graduate, graduate, and undergraduate students for their future careers in academia and the pharmaceutical or chemical industry.

Representative Publications

"An Efficient Formal Synthesis of (-)-Clavosolide A Featuring a "Mismatched" Stereoselective Oxocarbenium Reduction." Carrick, J. D.; Jennings, M. P. Org. Lett. 11, 769-772 (2009).

"Convergent Formal Syntheses of (±)-Brussonol and (±)-Abrotanone via an Intramolecular Marson-Type Cyclization." Martinez-Solorio, D.; Jennings, M. P. Org. Lett. 11, 189-192 (2009).

"Syntheses of epi-aigialomycin D and deoxy-aigialomycin C via a diastereoselective ring closing metathesis macrocyclization protocol." Bajwa, N.; Jennings, M. P. Tetrahedron Lett. 49, 390-393 (2008).

"Total Synthesis of (-)-Dactylolide and Formal Synthesis of (-)-Zampanolide via Target Oriented β-C-Glycoside Formation." Ding, F.; Jennings, M. P. J. Org. Chem. 73, 5965-5976 (2008).

"Vicinal Functionalization of Propiolate Esters via a Tandem Catalytic Carbocupration-Mukaiyama Aldol Reaction Sequence." Mueller, A. J.; Jennings, M. P. Org. Lett. 10, 1649-1652 (2008).

"Synthesis of the C17-25 subunit of lasonolide A utilizing a Tsuchihashi-Yamamoto type rearrangement." Sawant, K. B.; Ding, F.; Jennings, M. P. Tetrahedron Lett. 48, 5177-5180 (2007).

"Total Synthesis and Absolute Configuration Determination of (+)-Bruguierol C." Solorio, D. M.; Jennings, M. P. J. Org. Chem. 72, 6621-6623 (2007).

"Efficient Total Syntheses and Structural Verification of Both Diospongins A and B via a Common δ-Lactone Intermediate." Sawant, K. B.; Jennings, M. P. J. Org. Chem. 71, 7911-7914 (2006).

"An efficient synthesis of the C1-C14 subunit of (-)-lasonolide A via a target oriented β-C-glycoside formation sequence." Sawant, K. B.; Ding, F.; Jennings, M. P. Tetrahedron Lett. 47, 939-942 (2006).

"An efficient total synthesis and absolute configuration determination of varitriol." Clemens, R. T.; Jennings, M. P. Chem. Commun., 2720-2721 (2006).

Complete list of Dr. Jennings publications (2/10/09)

The University of Alabama Department of Chemistry Faculty