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.

Detailed 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.