Faculty Research Interests

Affiliates

Lecturers

Faculty Office Hours

Faculty Awards

NMR/Mass Spec Facilities

Reserve NMR

Reserve Mass Spec

X-Ray Facility

X-Ray Crystallography

Resources

Chemistry and Biochemistry
University of California
230 Physical Sciences Bldg.
Santa Cruz, CA 95064
Phone: (831) 459-4002
Fax: (831) 459-2935
Email
Maps & Directions

Joe Konopelski Professor of Chemistry B.A., M.A., Johns Hopkins University Ph.D., Stanford University Office: 344 PSB Phone: (831) 459-4676 Fax: (831) 459-2935 joek@chemistry.ucsc.edu

Konopelski Research Group Department of Chemistry University of California 1156 High Street Santa Cruz, CA 95064 Office Hours Class Times & Locations Labs: 379 PSB, 9-4669 Konopelski Research Group

RESEARCH INTERESTS: Organic Synthesis, Synthetic Methodology, Asymmetric Synthesis, Heterocycles, Bioorganic Chemistry

The focus of our research effort is the development of new synthetic methodologies and their application to the total synthesis of complex organic molecules. The rational design and execution of a multistep synthetic scheme remains one of the most challenging areas of chemistry. It requires not only a ready knowledge of organic transformations and sophisticated laboratory technique, but also a fundamental understanding of many other areas of chemistry, ranging from modern theory and reaction mechanism to organometallic chemistry.

These two research themes depend heavily on each other. The design and execution of the total synthesis of complex organic molecules, many of which have interesting biological activity and/or medicinal properties, is a primary research function in our laboratory.

Current synthetic projects include the cytotoxic marine natural product diazonamide A and the structurally unique alkaloid N-methylwelwitindolinone C isothiocyanate. Each of these targets is being pursued in enantiomerically pure form, since nature produces these important medicinal compounds as single enantiomers. Synthetic schemes are designed to allow entry into an entire class of compounds for ease of analog development.

New synthetic methodology goes hand in hand with total synthesis, as the ability to build complex molecular structure is only as good as the available tools, and the limits of those tools are tested and refined to the utmost in a total synthetic venture. Our interest in enantiomerically pure compounds has prompted the exploration into new methods for the synthesis of chiral nonracemic molecules. A key methodology in the synthesis of both of the indole alkaloids shown below is the use of organolead(IV) reagents. These aryl cation equivalents are versatile reagents, particularly in the formation of quaternary centers.

Likewise, we have extended the use of organolead reagents to the synthesis of unusual amino acids. One example of the ongoing work in our laboratory is the synthesis of the active site pentapeptide found in the redox enzyme cytochrome c oxidase. As can be seen from the diagram, this system contains an unusual side chain coupled amino acid that reacts the cyclic system. Our ongoing studies in this area are in collaboration with our colleague Professor Ólöf Einarsdóttir.

SELECTED PUBLICATIONS

Deng, H.; Konopelski, J.P., "Aryllead(IV) Reagents in Synthesis: Formation of the C11 Quaternary Center of N-Methylwelwitindolinone C Isothiocyanate," Org. Lett. 2001; 3; 3001-3004.

Elliott, G.I.; Konopelski, J.P., "Recent Trends in Arylation Reactions with Organolead and Organobismuth Reagents," Tetrahedron 2001, 57, 5683-5705 (Tetrahedron Report number 573).

Cappuccio, J.A.; Ayala, I.; Elliott, G.I.; Szundi, I.; Lewis, J.; Konopelski, J.P.; Barry, B.A.; Einarsdóttir, Ó., "Modeling the Active Site of Cytochrome Oxidase: Synthesis and Characterization of a Cross-linked Histidine-Phenol," J. Am. Chem. Soc. 2002, 124, 1750-60.