Synthesis of Luotonin A and its analogs by radical cascade cyclization

ORGN 398

Dennis P. Curran and Raghuram S. Tangirala. Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260
Luotonin A is a pyrroloquinazolinoquinoline alkaloid extracted from the Chinese medicinal plant Peganum nigellastrum by Nomura and coworkers in 1997. Luotonin A shows certain obvious structural similarities to camptothecin (CPT), the parent of an important class of anticancer agents. Luotonin A was also recently shown to mediate topoisomerase-I dependent cytotoxicity, akin to that shown by CPT. An approach to the synthesis of Luotonin A and its analogs using a radical cascade cyclization methodology will be presented. Rapid access to the analogs of Luotonin A using this approach allows for a quick study of its structure-activity relationships.

 

Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004