Research Synopsis: Computational & experimental mechanistic studies. New reaction discovery and method development. Synthesis of functional materials, including complex bio-active and natural products.
Phone: (848) 445-7916
Our research addresses a broad spectrum of problems at the interface of synthetic organic chemistry and biology. What inspires our work is the obsession with the idea that what has already been said about synthesis is still not enough. Thus in each of our projects we set out to demonstrate new - or to explore poorly understood - principles of chemical reactivity. Since we consider natural product total synthesis an opportunity to gain knowledge, our efforts in total synthesis are never finished they simply stop at interesting places.
Total synthesis as a tool for exploring biological activity
Our interests in medicine are derived from the profoundly selective events that many sophisticated organic molecules trigger in multi-cellular organisms. Hence, the synthesis of bioactive organic molecules enables complex biological processes to be scrutinized. In our current researches on the preparation and elaboration of non-ribosomal peptide, polyketide, and terpene natural products, each target has tantalizing, and only partially understood biological activity.
In all research we strive to maintain a global view of the relevance of our studies to science and medicine in general. For example, we actively seek out targets relevant to oncology and immunology. Indeed, what begins as a precise question regarding chemical reactivity and the subtle interplay between reactivity and molecular structure, proceeds with investigating the molecular requirements of biological activity and medicinal applications with the goal to register an advance in disease management.
- "Spirodiepoxides: Heterocycle Synthesis and Mechanistic Insight," with : Stephen D. Lotesta, Sezgin Kiren, Ronald R. Sauers, Angew.Chem. Int. Ed. (2007) 46, 15.
- "Synthesis of the C21–C28 segment of pectenotoxin-4," with : Robert V. Kolakowski, Tetrahedron Lett. (2007) 48(27), 4761.
- "A Formal Synthesis of Psymberin," with : Shangguan, N.; Kiren, S. Org.Lett. (2007) 9(6), 1093.
- "Spirodiepoxide Reaction with Cuprates," with : Ghosh, P.; Lotesta, S. D", J. Am. Chem. Soc., (2007) 129(9); 2438-2439
- "A Spirodiepoxide-Based Strategy to the A-B Ring System of Pectenotoxin 4," with : Lotesta, S. D.Org. Lett. (2007) 9(5), 869.
- "Mechanism of Thio Acid/Azide Amidation," with : Kolakowski, R. V.; Shangguan, N.; Sauers, R. R. J. Am. Chem. Soc (2006) 128(17), 5695.
- "Thio Acid/Azide Amidation: An Improved Route to N-Acyl Sulfonamides," with : Kristin N. Barlett, Robert V. Kolakowski, Sreenivas Katukojvala Org. Lett. (2006) 8(5), 823.
- "Thioamides via thiatriazolines," with : Robert V. Kolakowski, Ning Shangguan Tetrahedron. Lett. (2006) 47(7), 1163.
- "Configuration of the Psymberin Amide Side Chain," with : Kiren, Sezgin. Org. Lett. (2005) 7, 2905.
- "Spirodiepoxides in Total Synthesis: Epoxomicin," with : S. Katukojvala, K. Barlett, S. Lotesta J. Am. Chem. Soc. (2004) 126, 15348
- "The Reaction of Thioacids and Azides: A New Mechanism and New Applications," with :N. Shangguan, S. Katukojvala J. Am. Chem. Soc. (2003) 125, 7754