Professor

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

OFFICE
Beury Hall 442

MAILING ADDRESS
Department of Chemistry
Beury Hall 130
1901 N. 13th Street
Philadelphia, PA 19122

PHONE
office: 215-204-7916
fax: 215-204-1532
lab: 215-204-3037

E-MAIL
scott.sieburth@temple.edu

RESEARCH GROUP

http://astro.temple.edu/~sieburth/group.html

Medicinal / Organic

Research Interests

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.

Selected Publications

S Sen, M Purushotham, YM Qi, Scott McN. Sieburth, "Efficient asymmetric synthesis of silanediol precursors from 1,5-dihydrosiloles", Organic Letters, 2007, 9, 4963-4965.

PL Chen, PJ Carroll, Scott McN. Sieburth, "Intramolecular reactivity of trans [4+4] Photodimers of 2-Pyridones", Synthesis-Stuttgart, 2007, 15, 2351-2359.

PL Chen, YP Chen, PJ Carroll, Scott McN. Sieburth, "Novel Reaction Pathways for 2-pyridone [4+4] Photoadducts", Organic Letters, 2006, 8, 3367-3370.

CA Chen, Scott McN. Sieburth, "Silanediol Protease Inhibitors: From Conception to Validation", European Journal of Organic Chemistry, 2006, 2, 311-322.

DH Juers, J Kim, BW Matthews, Scott McN. Sieburth, "Structural Analysis of Silanediols as Transition-State-Analogue Inhibitors of the Benchmark Metalloprotease Thermolysin", Biochemistry, 2005, 44, 16524-16528.

Jaeseung Kim, Gregory Hewitt, Patrick Carroll and Scott McN. Sieburth, " Silanediol Inhibitors of Angiotensin-Converting Enzyme (ACE).   Synthesis and Evaluation of Four Diastereomers of Phe[Si]Ala Dipeptide Analogues", Journal of Organic Chemistry , 2005 , 70 , 5781-5789.

Guodong Liu and Scott McN. Sieburth, " a -Trialkylsilyl Amino Acid Stability."   Organic Letters , 2005 , 6 , 665-668.

Scott McN. Sieburth, "Photochemical Reactivity of Pyridones" in   CRC Handbook of Organic Photochemistry and Photobiology ,   W. Horspool, Ed., 2nd Ed., CRC, 2005, pp 103/1 - 103/18.

Jaeseung Kim and Scott McN. Sieburth, "Silanediol Peptidomimetics. Evaluation of Four Diastereomeric ACE Inhibitors.." Bioorganic and Medicinal Chemistry Letters , 2004 , 14 , 2853-2856.

Jaeseung Kim and Scott McN. Sieburth, "A Silanediol Inhibitor of the Metalloprotease Thermolysin: Synthesis and Comparison with a Phosphinic Acid Inhibitor." Journal of Organic Chemistry 2004 , 69 , 3008-3014.

Scott McN. Sieburth, "Photocycloaddition of alkenes (dienes) to dienes [4+4]/[4+4]" in   Synthetic Organic Photochemistry ,   A. G. Griesbeck and J. Mattay, eds., 2004, Chapter 9, 236-258.  

Scott McN. Sieburth, Heather K. O'Hare, Jiaji Xu, Yanping Chen and Guodong Liu, "Asymmetric Synthesis of a -Amino Allyl, Benzyl and Propargyl Silanes by Metalation and Rearrangement " Organic Letters 2003 , 5 , 1859-1861.

Guodong Liu and Scott McN. Sieburth, "Enantioselective a -Silyl Amino Acid Synthesis by Reverse-Aza-Brook Rearrangement."   Organic Letters 2003 , 5 , 4677 - 4679.