Scott McN. Sieburth
B.S. (1977), Worcester Polytechnic Institute
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.
S Singh, SM Sieburth, "Serine Protease Inhibition by a Silanediol Peptidomimetic ", Organic Letters, 2012, 14, 17, 4422-4425.
JK Kim, SM Sieburth, "Synthesis and Properties of a Sterically Unencumbered delta-Silanediol Amino Acid", Journal of Organic Chemistry, 2012, 77, 6, 2901-2906
L Chen, Y Lei, AG Shilabin, JD Delaney, GR Baran, SM Sieburth, "beta-Peptide coatings by surface-initiated polymerization", Chemical Communications, 2012, 48, 77, 9604-9606
S Kulyk, WG Dougherty, WS Kassel, MJ Zdilla, SM Sieburth, "Intramolecular Pyridone/Enyne Photocycloaddition: Partitioning of the [4+4] and [2+2] Pathways", Organic Letters, 2011, 13, 9, 2180-2183
YJ Bo, S Singh, HQ Duong, C Cao, SM Sieburth, "Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors", Organic Letters, 2011, 13, 7, 1787-1789
PL Chen, PJ Carroll, SM Sieburth, "Tetraquinanes via [4+4] Photocycloaddition/Transannular Ring Closure", Organic Letters, 2010, 12, 20, 4510-4512.
S Kulyk, WG Dougherty, WS Kassel, SM Sieburth, "Enyne [4+4] Photocycloaddition: Bridged 1,2,5-Cyclooctatrienes", Organic Letters, 2010, 12, 15, 3296-3299.
P Chen, PJ Carroll, SM Sieburth, "Bipiperidines via Sequential [4+4]-[3,3]-Retro-Mannich Reactions", Organic Letters, 2009, 11, 20, 4540-4543.
S Sen, S Singh, SM Sieburth, "A Practical, Two-Step Synthesis of 2-substituted 1,3-Butadienes", Journal of Organic Chemistry, 2009, 74, 7, 2884-2886.
S Sen, M Purushotham, YM Qi, SM Sieburth, "Efficient asymmetric synthesis of silanediol precursors from 1,5-dihydrosiloles", Organic Letters, 2007, 9, 4963-4965.
PL Chen, PJ Carroll, SM Sieburth, "Intramolecular reactivity of trans [4+4] Photodimers of 2-Pyridones", Synthesis-Stuttgart, 2007, 15, 2351-2359.