个人简介

B.S. (1977), Worcester Polytechnic Institute Ph.D. (1983) Harvard University

研究领域

Organic Chemistry

Synthetic Organic and Medicinal Chemistry Organosilicon 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. [4+4] Photocycloaddition 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.

近期论文

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PB Finn, S Kulyk, SM Sieburth, “Formation and isomerization of polyclic 1,5-enynes “, Tetrahedron Letters. 2015, in press. Link 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. BB Khatri, S Kulyk, SM Sieburth, “Enyne [4+4] photocycloaddition with polycyclic aromatics “, Organic Chemistry Frontiers. 2014, 1, 961-964. Link S Kulyk, BB Khatri, SM Sieburth, “Stabilization, Isomerization and Rearrangement of Enyne [4+4]-cycloadducts “, Organic Letters. 2014, 16, 4138-4141. Link Y Bo, PB Finn, BB Khatri, SM Sieburth, “Alpha-amino silanes via metalated imines as an approach to the synthesis of silanediol protease inhibitors “, Tetrahedron. 2013, 69, 7779-7784. Link S Singh, SM Sieburth, “Serine Protease Inhibition by a Silanediol Peptidomimetic “, Organic Letters. 2012, 14, 4422-4425. Link JK Kim, SM Sieburth, “Synthesis and Properties of a Sterically Unencumbered delta-Silanediol Amino Acid”, Journal of Organic Chemistry. 2012, 77, 2901-2906. Link L Chen, Y Lei, AG Shilabin, JD Delaney, GR Baran, SM Sieburth, “beta-Peptide coatings by surface-initiated polymerization”, Chemical Communications. 2012, 48, 9604-9606. Link 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, 2180-2183. Link YJ Bo, S Singh, HQ Duong, C Cao, SM Sieburth, “Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors”, Organic Letters. 2011, 13, 1787-1789. Link PL Chen, PJ Carroll, SM Sieburth, “Tetraquinanes via [4+4] Photocycloaddition/Transannular Ring Closure”, Organic Letters. 2010, 12, 4510-4512. Link S Kulyk, WG Dougherty, WS Kassel, SM Sieburth, “Enyne [4+4] Photocycloaddition: Bridged 1,2,5-Cyclooctatrienes”, Organic Letters. 2010, 12, 3296-3299. Link P Chen, PJ Carroll, SM Sieburth, “Bipiperidines via Sequential [4+4]-[3,3]-Retro-Mannich Reactions”, Organic Letters. 2009, 11, 4540-4543. Link S Sen, S Singh, SM Sieburth, “A Practical, Two-Step Synthesis of 2-substituted 1,3-Butadienes”, Journal of Organic Chemistry. 2009, 74, 2884-2886. Link S Sen, M Purushotham, YM Qi, SM Sieburth, “Efficient asymmetric synthesis of silanediol precursors from 1,5-dihydrosiloles”, Organic Letters. 2007, 9, 4963-4965. Link PL Chen, PJ Carroll, SM Sieburth, “Intramolecular reactivity of trans [4+4] Photodimers of 2-Pyridones”, Synthesis-Stuttgart. 2007, 15, 2351-2359. Link PL Chen, YP Chen, PJ Carroll, SM Sieburth, “Novel Reaction Pathways for 2-pyridone [4+4] Photoadducts”, Organic Letters. 2006, 8, 3367-3370. Link CA Chen, SM Sieburth, “Silanediol Protease Inhibitors: From Conception to Validation”, European Journal of Organic Chemistry. 2006, 2, 311-322. Link