Medicinal / Organic
Synthetic Organic and Medicinal Chemistry
Organosilane chemistry investigations include the study of silanediols as transition state analogue inhibitors of protease enzymes, such as thermolysin, angiotensin-converting enzyme (to lower blood pressure), HIV protease (AIDS treatment), anthrax lethal factor (as a cure for anthrax infection), matrix metalloprotease (applications to cancer and other diseases). more information...
Related areas of organosilicon chemistry include the synthesis and study of a-silyl amino acids and their use in medicinal chemistry and peptide conformation, and the development of novel organosilane reagents.
2-Pyridones undergo efficient [4+4] photocycloaddition with themselves and with 1,3-dienes, furans and naphthalenes. The resulting adducts are functional group rich and overlap with a variety of natural products, including eight-membered ring structures like taxol and the fusicoccins. The rigid, densely functionalized structures also undergo transannular reactions, such as during the chlorination shown. Our studies involve both fundamental reactivity issues and total synthesis.
Paul B. Finn, Svitlana Kulyk and Scott McN. Sieburth, "Formation and isomerization of polycyclic 1,5-enynes" Tetrahedron Letters, 2015, in the press.
Scott McN. Sieburth "Bioactive Amino Acids, Peptides and Peptidomimetics Containing Silicon", in Bio-Inspired Silicon-Based Materials, P. M. Zelisko, Ed.; Springer, New York, (2014), 103-123.
Scott McN. Sieburth "Silicon Mimics of Unstable Carbon", in Atypical Elements in Drug Design, Jacob Schwarz, Ed.; Springer, New York, 2014.
Svitlana Kulyk, Buddha B. Khatri and Scott McN. Sieburth, "Stabilization, Isomerization and Rearrangement of Enyne [4+4] Cycloadducts" Organic Letters, (2014), 16, 4138–4141.
Buddha B. Khatri, Svitlana Kulyk and Scott McN. Sieburth, "Enyne [4+4] Photocycloaddi-tion with Polycyclic Aromatics" Organic Chemistry Frontiers, (2014), 1, 961-964.
Yingjian Bo, Paul B. Finn, Buddha B. Khatri and Scott McN. Sieburth, "Alpha-amino silanes via metalated imines as an approach to the synthesis of silanediol protease inhibitors" Tetrahedron, (2013), 69, 7779-7784.
Jin Kyung Kim and Scott McN. Sieburth, "Synthesis and Properties of a Sterically Unencumbered δ-Silanediol Amino Acid" The Journal of Organic Chemistry, (2012), 77, 2901−2906. DOI: 10.1021/jo300175t
Li Chen, Yong Lei, Abbas G. Shilabin, James D. Delaney, George R. Baran and Scott McN. Sieburth, "β-Peptide Coatings by Surface-Initiated Polymerization" Chemical Communications, (2012), 48, 9604-9606.
Swapnil Singh and Scott McN. Sieburth, "Serine Protease Inhibition by a Silanediol Peptidomimetic" Organic Letters, 2012, 14, 4422-4425.
Yingjian Bo, Swapnil Singh, Hoan Quoc Duong, Cui Cao and Scott McN. Sieburth, "Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors" Organic Letters, (2011), 13, 1787–1789.
Svitlana Kulyk, William G. Dougherty, Jr., W. Scott Kassel, Michael J. Zdilla and Scott McN. Sieburth, "Intramolecular Pyridone/Enyne Photocycloaddition: Partitioning of the [4 + 4] & [2 + 2] Pathways" Organic Letters, (2011), 13, 2180-2183.
Svitlana Kulyk, William G. Dougherty, Jr., W. Scott Kassel, Steven A. Fleming, and Scott McN. Sieburth, "Enyne [4 + 4] Photocycloaddition: Bridged 1,2,5-Cyclooctatrienes" Organic Letters, (2010), 12, 3296-3299.
Peiling Chen, Patrick J. Carroll and Scott McN. Sieburth, "Tetraquinanes via [4+4] Photocycloaddition / Transannular Ring Closure" Organic Letters, (2010), 12, 4510-4512.