Professor of Chemistry[email protected] 413-597-2354
Lab: Morley Science Laboratory, Room 150
Ph.D. Stanford University, Organic Chemistry (1996)
Postdoctoral Fellow at Harvard University (1998)
Areas of Expertise
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.
- Smith, Thomas E.; Fink, Sarah J., Levine, Zebulon G.; McClelland, Kerani A.; Zachheim, Adrian A.; Daub, Mary E. “Stereochemistry Versatile Synthesis of the C1–C12 Fragment of Tedanolid C” Org. Lett. 2012, 14, 1452-1455.
- 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.
Previous Courses Taught
- 111: Fighting Disease: The Evolution and Operation of Human Medicines
- 156: Organic Chemistry: Introductory Level
- 342: Synthetic Organic Chemistry
- 343: Medicinal Chemistry
Honors Research Students
Former Group Members
Summer 2010: Rachel Patel ’12, Mary Beth Daub ’11, Menghan Zhao ’13, Zeb Levine ’11, and Mark Johnson ’11
Pacifichem 2000, Honolulu, HI
Vicky Bock ’04 and Jennifer Roizen ’03 with their Hennoxazole cake.
- Carly Schissel ’16
- Ashley Kim ’15, Research Assistant, Theravance Biopharma
- Zaw-htut Naing ’15, Research Technician, Boston University Medical School
- Craig Burt ’14, University of California, Irvine
- Mika Nakashige ’13, Dartmouth College
- Menghan Zhao ’13, Clinical Research Coordinator, Faustman Lab at MA General Hospital
- Rachel Patel ’12, University of Massachusetts Medical School
- Mary Beth Daub ’11, University of California, Irvin, Graduate School in organic chemistry (Ph.D. advisor: TBA)
- Marian Deuker ’11, University of California, San Francisco, Graduate School in chemistry (Ph.D. advisor: TBA)
- Mark Johnson ’11, Olympic Training Facility (Biathalon), applying to medical school
- Zebulon Levine ’11, Herschel Smith Fellow, Cambridge University (M.Phil Advisor: Steven Ley)
- Amanda Huey ’10, Research Associate, NIH, applying to medical school
- Edwin Layng ’10, applying to medical school
- Kerani McClelland ’10, applying to medical school
- Caleb Weatherly ’09, University of Wisconsin Graduate School in organic chemistry (Ph.D. Advisor: Jennifer Schomaker)
- Alex Zackheim ’09, Financial Analyst
- Sarah J. Fink ’09, Herchel Smith Fellowship, Cambridge University (D.Phil. Advisor: Ian Paterson)
- Wen-Hsin Kuo ’06, Harvard University (Ph.D. Advisor: Eric Jacobsen)
- Ashleigh Theberge ’06, Herchel Smith Fellowship, Cambridge University (D. Phil. Advisor: Wilhelm Huck)
- Pamela Choi ’05, Robert Wood Johnson Medical School
- Salem Fevier ’05, Medicinal Chemist, Infinity Pharmaceuticals (one year) then Medicinal Chemist, Schering-Plough
- Victoria Bock ’04, University of Amsterdam International Master’s Program in Molecular Design, Synthesis and Catalysis. Currently: Analytical Laboratory Director, Brunei.
- Adrian Dowst ’04, Process Chemist, Merck & Co., Rahway, NJ; then University of Washington (Ph.D. Advisor: TBA)
- Jennifer L. Roizen ’03, CalTech (Ph.D. Advisor: Brian M. Stoltz)
- Emily P. Blaskus ’02 (class Valedictorian), Winston Churchill Fellow, Cambridge University (M.Phil. Advisor: Steven Ley); NSF Predoctoral Fellow, Harvard University (Ph.D. Advisor: Eric Jacobsen), NIH Postdoctoral Fellow, Harvard Medical School (Postdoctoral Advisor: Chris Walsh); Assistant Professor of Chemistry, Harvard University
- Alan J. Velander ’02, University of Michigan Medical School
- Katherine Belecki ’01, Discovery Chemist, Pfizer Central Research, Groton, CT; then Johns Hopkins (Ph.D. Advisor: Craig Townsend)
- Mabel Djang ’01, Discovery Chemist, Pfizer Central Research, Groton, CT; then Harvard Medical School
- Michelle S. Mourad ’00, New York University Medical School
- Carolyn A. Stickney ’00, Case Western Medical School
- James P. Sieradzki ’99, Washington University, St. Louis Medical School
- Scott A. Snyder ’99 (class Valedictorian), Scripps Research Institute (Ph.D. Advisor: K.C. Nicolaou); NIH Postdoctoral Fellow, Harvard University (Postdoctoral Advisor: E. J. Corey), Assistant Professor, Columbia University
- Committee on Appointments and Promotions