Kwon, Ohyun


WebsiteHome URL
Division
Organic
Title
Faculty
Professor
Specialties
Organic
Chemical Biology
Synthesis

Contact Information

Email
Office
Molecular Sciences Building 3505C
(310) 267-4954
Lab
Molecular Sciences Building 3235
(310) 206-9648

Short Biography

Professor Kwon received her B.S. degree in 1991 at Seoul National University in Korea, and her PhD in 1998 from Columbia University. After the postdoctoral stint at Harvard University, she joined the faculty at UCLA in 2001.

Biography

Ohyun Kwon received her B.S. (1991) and M.S. (1993) from Seoul National University in South Korea. In 1993, she came to the U.S. to pursue her Ph.D. (1998) from Columbia University under the guidance of S. J. Danishefsky. Her thesis work involved the synthesis of biologically significant glycolipid, asialo GM1 and Globo-H human breast tumor antigen molecule, as well as complex phomoidride terpenoids, CP-225,917 and CP-263,114. She then went to Harvard University as a Howard Hughes Postdoctoral Fellow to study chemical genetics in S. L. Schreiber's lab. There, she completed a diversity-oriented combinatorial synthesis (DOS) of a library of muticyclic compounds, as well as a library of macrocycles. Kwon joined the faculty as an assistant professor at UCLA in 2001. She has been a member of the Molecular Biology Institute (MBI) and UCLA Jonsson Comprehensive Cancer Center (JCCC) since 2005. Her research at UCLA evolves around the development of new nucleophilic phosphine catalysis reactions. The new reaction methodologies are used in the total synthesis of natural products and in the production of libraies of small organic molecules for chemical genetic applications.

Research Interest

Our research interest lies in the area of development of new methodologies for organic transformations, target oriented synthesis of biologically important natural compounds, and diversity oriented synthesis of natural product-like molecules. Molecules thus built will be employed in the investigation of biologically significant processes. Each project described below encompasses more than one area of these research interests.

A Proposed Synthesis of Antinociceptive Resiniferatoxin

In its practice, developing new organic transformations is multifaceted. As part of our endeavor to synthesize resiniferatoxin, a "vinylogous pinacol rearrangement" is proposed for the construction of hydroazulene system from trans -decalin framework. This new reaction is of critical use for the synthesis of resiniferatoxin.

Syntheses of 2-Deoxy-2-Amino Sugars

A universal method to synthesize various natural and unnatural glycosamines from their anhydrous sugar precursors is another area of interest. With the unparalleled expansion of our understanding in glycobiology over the past decade, there is no better time for this effort.

Diversity Oriented Synthesis of Chiral Multicyclic Compounds based on Asymmetric Organic Catalysis

Asymmetric organic catalysis is drawing much attention in recent years. Simplicity and environmental friendliness in its practice are two of many advantages that organic catalysis renders. Catalytic amount of single organic molecule is used to furnish a series of enantiomerically pure organic molecules. The single asymmetric center in the dihydrofuran thus created will control the face from which dienophiles approach the diene. Thereby, a library of enantiomerically pure tricyclic compounds will arise.

 

Asymmetric Syntheses of MDR Antibiotic Guanacastepene A and the Combinatorial Synthesis of its Analogs

Emergence of vancomycin-resistant Enterococcus (VRE) in conjunction with methhicillin-resistant S. aureus (MRSA) has become a tremendous threat to human health since vancomycin has been the last resort for treating infections caused by MRSA. Isolation of guanacastepene A and its antibiotic activity against MRSA and VRE has attracted many interests in the synthetic community. We are also involved in the concise 14-step synthesis of guanacastepene A. Unfortunately, guanacastepene A demonstrates hemolytic activity as well as its activity against multi drug-resistant strains of pathogenic bacteria. Our plan is to apply the scheme developed in its total synthesis to the solid-phase split-pool synthesis of guanacastepene analogs. Combined with comparative assays against red blood cells and pathogenic bacteria, a library of guanacastepene A-like compounds presents a possibility of discovering a new multi drug-resistant antibiotic.

Honors & Awards

Amgen Young Investigator's Award
Synthesis and Synlett Thieme Journal Award
UCLA Faculty Career Development Award
Glenn T. Seaborg Award
Columbia University KAST Fellowship

Publications

Lu, J.; Chan, L.; Fiji, H. D. G.; Dahl, R.; Kwon, O.; Tamanoi, F   In vivo anticancer effect of a novel inhibitor of protein geranylgeranyltransferase I, Mol. Cancer Ther., 2009; 8: 1218-1226.
Guo, H.; Xu, Q.; Kwon, O.   Phosphine-Promoted [3+3] Annulation of Aziridines with Allenoates: A Facile Entry into Highly Functionalized Tetrahydropyridines, J. Am. Chem. Soc, 2009; 131: 6318-6319.
Creech, G. S.; Kwon, O.   Alcohol-Assisted Phosphine Catalysis: One-Step Synthesis of Dihydropyrone from Aldehyde and Allenoate, Org. Lett., 2008; 10: 429?432.
Andrews, I.P., Kwon, O.   Highly Efficient Palladium-Catalyzed Hydrostannation of Ethyl Ethynyl Ether Tetrahedron Lett., 2008; 49: 7097-7099.
Watanabe, M.; Fiji, H. D. G.; Guo, L.; Umetsu, A.; Kinderman, S. S.; Slamon, D. J.; Kwon, O.; Tamanoi, F.   Inhibitors of protein geranylgeranyltransferase-I and Rab geranylgeranyltransferase identified from a library of allenoate derived compounds, J. Biol. Chem., 2008; 283: 9571?9579.
Creech, G. S.; Zhu, X.; Fonovic, B.; Dudding, T.; Kwon, O.   Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates, Tetrahedron, 2008; 64: 6935?6942.
Sriramurthy, V.; Barcan, G. A.; Kwon, O.   Bisphosphine-Catalyzed Mixed Double-Michael Reactions: Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines, J. Am. Chem. Soc., 2007; 129: 12928?12929 (Highlighted in SYNFACTS 2008, 19; Featured as a Synstory in SYNFORM 2008, A10?A12).
Mercier, E.; Fonovic, B.; Henry, C. E.; Kwon, O.; Dudding, T.   Phosphine Triggered [3+2] Allenoate-Acrylate Annulation: A Mechanistic Enlightenment, Tetrahedron Lett., 2007; 48: 3617?3620.
Henry, C. E.; Kwon, O.   Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins, Org. Lett., 2007; 9: 3069?3072 (Highlighted in SYNFACTS 2007, 1145).
Tran, Y. S.; Kwon, O.   Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Cyclohexenes, J. Am. Chem. Soc., 2007; 129: 12632?12633.
Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; De Leon, P.; Tamanoi, F.; Kwon, O.   Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I, J. Am. Chem. Soc., 2007; 129: 5843?5845.
Zhu, X.; Henry, C. E.; Kwon, O.   Stable Tetravalent Phosphonium Enolate Zwitterions, J. Am. Chem. Soc., 2007; 129: 6722?6723.
Dudding, T.; Kwon, O.; Mercier, E.   Theoretical Rationale for Regioselection in Phosphine Catalyzed Allenoate Additions to Acrylates, Imines and Aldehydes, Org. Lett., 2006; 8: 3643?3646.
Zhu, X.-F.; Henry, C. E.; Kwon, O.   A highly diastereoselective synthesis of 3-carbethoxy-2,5-disubstituted-3-pyrrolines by phosphine catalysis, Tetrahedron, 2005; 61: 6276-6282.
Tran, Y. S.; Kwon, O.   An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline, Org. Lett., 2005; 7: 4289?4291.
Zhu, X.-F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O.   Phosphine-Catalyzed Synthesis of 1,3- Dioxan-4-ylidenes, Org. Lett., 2005; 7: 1387-1390.
Zhu, X.-F.; Schaffner, A.-P.; Li, R. C.; Kwon, O.   Phosphine-Catalyzed Synthesis of 6-Substituted 2-pyrones: Manifestation of E/Z-Isomerism in the Zwitterionic Intermediate, Org. Lett., 2005; 7: 2977-2980.
Du, X.; Chu, H. V.; Kwon, O.   A Concise Synthesis of the Functionalized [5-7-6] Tricyclic Skeleton of Guanacastepene A, Tetrahedron Lett., 2004; 6: 8843-8846.
Schmidt, D.R.; Kwon, O.; Schreiber, S.L.   Macrolactones in Diversity-Oriented Synthesis: Preparation of a Pilot Library and Exploration of Factors Controlling Macrocyclization, J. Comb. Chem., 2004; 6: 286-292.
Zhu, X.-F.; Lan, J.; Kwon, O.   An Expedient Phosphine-Catalyzed [4+2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines, J. Am. Chem. Soc., 2003; 125: 4716-4717.
Du, X.; Chu, H. V.; Kwon, O.   Synthesis of the [5-7-6] Tricyclic Core of Guanacastepene A via an Intramolecular Mukaiyama Aldol Reaction, Org. Lett., 2003; 5: 1923-1926.