Associate Professor of Chemistry
at Williams since 1998
Smith, Thomas E.; Richardson, David P.; Truran, George A.; Belecki, Katherine; Onishi, Megumi "Acylation, Diastereoselective Alkylation, and Cleavage of an Oxazolidinone Chiral Auxiliary: A Mulitistep Asymmetric Synthesis Experiment for Advanced Undergraduates" J. Chem. Educ. 2008, 85, 695-697.
Smith, Thomas E.; Kuo, Wen-Hsin; Balskus, ,Emily P.; Bock, Victoria D.; Roizen, Jennifer L.; Theberge, Ashleigh B.; Carroll, Kathleen A.; Kurihara, Tomoki; Wessler, Jeffrey D. "Total Synthesis of (–)-Hennoxazole A" J. Org. Chem. 2008, 73, 142-150.
Smith, Thomas E.; Kuo, Wen-Hsin; Bock, Victoria D.; Roizen, Jennifer L.; Balskus, Emily P.; Theberge, Ashleigh B. "Total Synthesis of (–)-Hennoxazole A" Org. Lett. 2007, 9, 1153-1155.
Smith, Thomas E.; Djang, Mabel; Velander, Alan J.; Downey, C. Wade; Carroll,
Kathleen A.; van Alphen, Sophie "Versatile Asymmetric Synthesis of the
Kavalactones: The First Synthesis of (+)-Kavain" Org. Lett. 2004, 6, 2317-2320.
Smith, Thomas E.; Balskus, Emily P. "Synthetic Studies Toward Hennoxazole A.
Use of a Selective Bisoxazole Alkylation as the Key Fragment Coupling" Heterocycles
2002, 57, 1219-1225.
Smith, Thomas E.; Mourad, Michelle S.; Velander, Alan J. "Effects of Base,
Electrophile, and Substrate on the Selective Alkylation of Heteroaromatic Systems"
Heterocycles 2002, 57, 1211-1217.
Evans, David. A.; Fitch, Duke M.; Smith, Thomas E.; Cee, Victor J. "Application
of Complex Aldol Reactions to the Total Synthesis of Phorboxazole B" J. Am.
Chem. Soc. 2000, 122, 10033-10046.
Evans, David. A.; Cee, Victor J.; Smith, Thomas E.; Fitch, Duke M.; Cho, Patricia
S. "Asymmetric Synthesis of Phorboxazole B, Part I: Synthesis of the C20-C38 and C39-C46 Subunits" Angew.
Chem., Int. Ed. Engl. 2000, 39, 2533-2536.
Evans, David. A.; Cee, Victor J.; Smith, Thomas E.; Santiago, Keith J. "Selective
Lithiation of 2-Methyloxazoles. Applications to Pivotal Bond Constructions in
the Phorboxazole Nucleus" Org. Lett. 1999, 1, 83.
Wender, Paul A.; Smith, Thomas E. "Transition Metal-Catalyzed Intramolecular
[4 + 2] Cycloadditions: Mechanistic and Synthetic Investigations" Tetrahedron
1998, 54, 1255-1275.
Wender, Paul A.; Smith, Thomas E. "Transition Metal-Catalyzed Intramolecular
[4 + 2] Cycloadditions: A Novel Method for the Assembly of Nitrogen Heterocycles
and Its Application to Yohimban Alkaloid Synthesis" J. Org. Chem. 1996,
61, 824-825.
Wender, Paul A.; Smith, Thomas E. "Transition Metal-Catalyzed Intramolecular
[4 + 2] Cycloadditions: Initial Studies on Stereochemistry and on Steroid and
Vitamin D Analog Syntheses" J. Org. Chem. 1995, 60, 2962-2963.
Richardson, David P.; Carr, Priscilla, W.; Cumming, Jared, N.; Harbison, W.
G.; Raoof, Nina D.; Sanders, Michelle S.; Shin, Eliza; Smith, Thomas E.; Wintner,
Thomas H. "Stereoselective Synthesis of 7R-Paeonimetaboline-I; Stereoselective
Route Towards Paeonifloigenone" Tetrahedron Lett. 1997, 38,
3817-3820.
Richardson, David P.; Smith, Thomas E.; Lin, William W.; Kiser, Cynthia N.;
Mahon, Brian R. "Stereoselective Synthesis of Paonilactones A, B and C," Tetrahedron
Lett. 1990, 31, 5973.
My research interests lie within the broad category of organic synthesis. Synthesis plays a central role in organic chemistry, and advances in this area impact upon a wide variety of investigations at the molecular level including those relating to biology, pharmacology, materials science, and reaction mechanism. My current focus is on the development of new methods for increased efficiency in organic synthesis and their application to molecules of biological significance. Organotransition metal systems, in particular, are utilized extensively in this endeavor due to their versatile selectivity profiles and catalytic possibilities.
In one project, we are exploring a general asymmetric synthesis of the kavalactones. These natural products are the biologically active constituents of kava root, which has been used ceremonially in South Pacific cultures for centuries and has attracted recent attention in the Western world as an "alternative" anti-anxiety remedy. We are also investigating the asymmetric total synthesis of the myxobacterial antibiotic, jerangolid D, wherein both the δ-lactone and cis-dihydropyran rings are assembled using an extension of the methods developed for the kavalactone syntheses. In another project we are probing the scope and limitations of a new method for the thermodynamic deprotonation of readily available heterocyclic systems, thus allowing for the assembly of more complex molecular architectures from simple building blocks. This technique was successfully applied to a novel synthesis of the antiviral marine natural product, hennoxazole A.
Pacifichem 2000, Honolulu, HI
Vicky Bock '04 and Jennifer Roizen '03 with their Hennoxazole cake.
Summer 2004