Intramolecular Diels-Alder reactions of vinylimidazoles: Approach to ageliferin and nagelamide E

ORGN 617

Carl J. Lovely, lovely@uta.edu, Yong He, Sivappa Rasappali, and Remond Moningka. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019
Our group had a long standing interest in developing new methods for the functionalization of imidazoles. As part of this effort, the intramolecular Diels-Alder chemistry of 4-vinylimidazoles has been investigated. These studies have led to efficient methods for the construction the requisite substrates 1 and the demonstration of successful cycloaddition for large number of these substrates. This presentation will detail the scope and limitations of these reactions, along with studies of a variety of linkers (X = O, NR, O-NR, N-N). Also to be discussed is the application of this methodolgy to the total synthesis of the oroidin-derived alkaloids, ageliferin (2) and nagelamide E (3).

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005