Synthetic studies towards Palau'amine and related compounds

ORGN 51

Carl J. Lovely, lovely@uta.edu, Sivappa Rasappali, Hongwang Du, and Heather Fenton. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019
Palau'amine (1) and other related dimeric oroidin-derived alkaloids have steadily attracted the attention of a number of synthetic groups over the last few years. Our own group became interested in these heterocyclic natural products due to our on-going programs in imidazole chemistry. We have extensively investigated the Diels-Alder chemistry of vinylimidazoles and the synthetic utility of the thus obtained adducts, and as a result have developed a concise approach towards the spiro fused DEF-rings. Our most recent work has focused on the preparation of significantly more elaborate substrates 2, which when subjected to the Diels-Alder/oxidative rearrangement chemistry developed in our labs should, provide rapid access to entire polycyclic framework found in palau'amine. This presentation will describe our current efforts towards these goals.