Daesung Lee
Publications | Awards |
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Assistant Professor, Born 1962
B.Sc. 1988, Seoul National University, Korea
M.Sc. 1990, Seoul National University, Korea
Ph.D. 1998, Stanford University
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1. Truc M. Nguyen, Robert J. Seifert, Dale R. Mowrey and Daesung Lee “Synthesis of the 5-7-6 Core of Guanacastepenes. Construction of C8 Quaternary Carbon via the Inversion of Stereochemistry” Org. Lett. 2002, 4, 3959–3962.
2. Truc M. Nguyen and Daesung Lee “Novel Reactivity of SeO2 with 1,3-Dienes: Selenophene Formation” J. Org. Chem. 2002, 67, 6553–6556.
3. Sarah V. Maifeld, Reagan L. Miller and Daesung Lee “Activation of Silanes by Grubbs’ Carbene Complex Cl2(PCy3)2Ru=CHPh: Dehydrogenative Condensation of Alcohols and Hydrosilylation of Carbonyls” Tetrahedron Lett. 2002, 43, 6363–6366.
4. Truc M. Nguyen and Daesung Lee “Progress Towards the Total Synthesis of Guanacastepene A. Approaches to the Construction of Quaternary Carbons and the 5-7-6 Tricyclic Carbon Skeleton” Tetrahedron Lett. 2002, 43, 4033–4036.
5. Truc M. Nguyen and Daesung Lee “A Novel Reactivity of SeO2 with 1,3-Dienes: Formation of Syn 1,2- and 1,4-Diols via a Facile C-Se Bond Oxidation” Org. Lett. 2001, 3, 3161–3163.
6. Daesung Lee, Jason Sello, Stuart L. Schreiber “Pairwise Use of Complexity-Generating Reactions in Diversity-Oriented Organic Synthesis” Org. Lett. 2000, 2, 709–712.
7. Daesung Lee, Jason Sello, Stuart L. Schreiber “A Strategy for Macrocyclic Ring Closure and Functionalization Aimed Towards Split-Pool Syntheses” J. Am. Chem. Soc. 1999, 121, 10648–10649.
8. Paul A. Wender, Neil F. Badham, Simon P. Conway, Paul E. Floreancig, Timothy E. Glass, Christian Gränicher, Jonathan B. Houze, Jan Jänichen, Daesung Lee et al. “The Pinene Path to Taxanes. 5. Stereocontrolled Synthesis of a Versatile Taxane Precursor” J. Am. Chem. Soc. 1997, 119, 2755–2756.
9. Paul A. Wender, Neil F. Badham, Simon P. Conway, Paul E. Floreancig, Timothy E. Glass, Jonathan B. Houze, Nancy E. Krauss, Daesung Lee et al. “The Pinene Path to Taxanes. 6. A Concise Stereocontrolled Synthesis of Taxol ®” J. Am. Chem. Soc. 1997, 119, 2757–2758.
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Research Interests: Total synthesis of biologically active natural products; development of new reactions and methodologies for the synthesis of natural and unnatural compounds; combinatorial chemistry.
Research Description: The development of efficient synthetic strategies for the synthesis of complex and diverse molecular structures will lie at the center of our research. These strategies will be applied to the total synthesis of biologically active natural compounds and also to the synthesis of chemical libraries of natural product-like compounds, which will then be screened in search of biologically interesting molecules. Ultimately, the biologically active subset of these molecules will be further developed as reagents to explore biological processes. New reactions and methodology development: Recently, we discovered new synthetic transformations that can be readily applicable to the synthesis of natural products and combinatorial libraries. These reactions include the synthesis of 1,2- or 1,4-diols from 1,3-dienes and functionalized biphenyls from a,b-unsaturated enones. We are developing a boron atom-assisted Cope rearrangement to construct a vinyl boronate bearing 1,5-diene functionality, a useful building block in many synthetic transformations. We are also interested in developing a bi-directional synthesis approach for polyketide synthesis especially polypropionate with defined absolute and relative stereochemistry.
Natural product synthesis: Despite the current state-of-the-art technologies in organic synthesis, growing member of new target molecules isolated from Nature require the development of new synthetic methods and strategies. We are currently developing new synthetic strategies for the total synthesis of those recently isolated natural compounds which include a potent immunosuppressant FR901483, an NF-kB inhibitor cycloepoxydone, and an antibiotic guanacastepene.
Multi-component coupling reactions (MCC) and combinatorial chemistry: A variety of MCC reactions are heavily used in combinatorial chemistry due to their capacity of generating complex and diverse array of molecules from simple building blocks. Our interest in this area is to discover new MCC reactions as well as to expand the scope of known MCC reactions for example, development of catalytic asymmetric Ugi reaction. Another potential application of Ugi reaction is to generate cyclic peptide-like macrocycles under the principles of macrocyclic stereocontrol. This strategy involves an initial formation of the conformationally well-defined cyclic imines followed by stereoselective addition of isonitrile from the outside of the macrocycle. This approach is well suited for the construction of libraries of cyclic peptide-like molecules. We are also interested in generating focused chemical libraries containing sphingolipid-related structures aiming for finding unnatural small molecule modulators for the sphingosine biosynthesis pathway.
Last updated March 1, 2001.
1. Camille and Henry Dreyfus New Faculty Award, 2000
2. Syntex Graduate Research Fellowship, 1993
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