The focus of our research program is the development of synthetic organic methods and their application to the synthesis of therapeutically important compounds. Our efforts are concentrated in several areas:
- The total synthesis of complex natural products and related analogs for structure activity relationship studies: the molecular targets we choose to pursue in these synthetic studies are expected to deepen our understanding of the biological process in which they intervene.
The development of expedited synthesis techniques to facilitate small-molecule library production: In this aspect of
we look at ways to simplify the process of making molecules by developing a variety of new methods both on polymer support and in solution.
Nucleophile assisting leaving groups (NALGs) for increased speed and precision in molecular construction: we have identified new reactions enabled by chelating leaving groups including fast radiolabeling with F18 for medical imaging applications (PET).
A Direct and Stereoretentive Synthesis of Amides from Cyclic Alcohols.
Mondal, D.; Bellucci, L.; Lepore, S.D. Eur. J. Org. Chem. 2011 (accepted).
Catalytic synthesis of non-racemic azaproline derivatives via a kinetic-resolution based cyclization of ß-alkynyl hydrazines. Maity, P.; Lepore, S.D. Angew. Chem. Int. Ed. 2011, 50, 8338.
Manganese n2-Complexes as Auxiliaries for Stereoselective Aldol Synthesis of Allenyl Carbinols. Bhowmick, M.; Lepore, S. D. Organic Lett 2010, 12, 5078.
Efficient Synthesis of Fmoc-Protected Phosphinic Pseudodipeptides: Building Blocks for the Synthesis of Matrix Metalloproteinase Inhibitors (MMPIs). Bhowmick, M.; Sappidi, R.; Fields, G.B.; Lepore, S. D. Biopolymers (Peptide Science) 2010, 6, 1.
Nucleophile Assisting Leaving Groups: A Strategy for Aliphatic 18F-Fluorination. Lu, S.-Y.; Lepore, S. D.; Li, S. Y.; Mondal, D.; Cohn, P. C.; Bhunia, A. K.; Pike, V. W. J. Org. Chem.2009, 74, 5290.
Anion Catalyzed Addition of g -Silylallenyl Esters to Aldehydes: A New Entry into [3.2.1] Bicyclic Natural Products. Maity, P.; Lepore , S.D. J. Am. Chem. Soc.2009, 131, 4196.
Selective One-Pot Synthesis of Allenyl and Alkynyl Esters from b -Ketoesters. Maity, P.; Lepore , S.D. J. Org. Chem. 2009 , 74, 158.
Stereoretentive Halogenations and Azidations with Titanium(IV) Enabled by Chelating Leaving Groups. Lepore, S.D.; Mondal, D.; Li, S.Y.; Bhunia, A.K. Angew. Chem. Int. Ed. 2008 , 47, 7511. (highlighted in SynForm2009, 2, A16 )
(18F)Fluorination of Alkyl Sulfonate is Enhanced by Arylsulfonate-Based Nucleophile Assisting Leaving Groups (NALGs) Under Microwave Irradiation. Lu, S. Y.; Li, S. Y.; Lepore, S. D.; Pike, V. W. J. Labelled Compd. Radiopharm.2007, 50 (Suppl. I), S5.
Recent Advances in Heterolytic Nucleofugal
Leaving Groups. Lepore, S.D.; Mondal, D. Tetrahedron 2007, 63, 5103-5122.
Rapid Conversion of Hindered Arylsulfonates to
Alkyl Chlorides with Retention of Configuration. Lepore, S.D.; Bhunia, A.K.; Mondal, D.; Cohn, P.C.; Lefkowitz, C. J. Org. Chem. 2006, 71, 3285.
Synthesis of Methyl 2-Oxo-5-Vinyl-2,5-Tetrahydrofuran-3-Carboxylate.
Silvestri, M.A.; He, C.; Khoram, A.; Lepore, S.D. Tetrahedron Lett., 2006, 47 1625.
Arylsulfonate Based Nucleophile Assisting Leaving Groups (NALGs).
Lepore, S.D.; Bhunia, A.K.; Cohn, P. J. Org. Chem. 2005, 70, 8117.
Michael-Stork Addition of Cyclopentyl Enamine to Allenyl Ketones and Esters.
Silvestri, M.A.; Bromfield, D.C.; Lepore, S.D. J. Org. Chem. 2005, 70, 8239.
Studies on the Manganese Mediated Isomerization of Alkynyl Carbonyls to Allenyl
Carbonyls. Lepore, S.D.; Khoram, A.; Bromfield, D.C.; Cohn, P.; Jairaj, V.; Silvestri, M.A. J. Org. Chem. 2005, 70, 7443.
Deconjugative Conversion of alpha-Alkynyl Esters to alpha,alpha-Disubstituted
beta-Alkynyl Esters. Lepore, S.D.; He, Y.J. J. Org. Chem. 2005, 70, 4546.
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