Investigation of a novel double barrelled Heck reaction involving pyrroles

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Courtney E. Rogers, rogersce@hendrix.edu1, Christina N. Barnes, goodwin@hendrix.edu1, Daniel Z. Liu, Goodwin@hendrix.edu1, Thomas E. Goodwin, goodwin@hendrix.edu1, and Martin G. Banwell2. (1) Department of Chemistry, Hendrix College, 1600 Washington Ave, Conway, AR 72032, (2) Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia
Banwell et al. (Aust. J. Chem., 1998, 52, 755) reported a unique “double-barrelled” Heck cyclization (1 to 2) to prepare an analog of the potent lamellarin class of anti-cancer, marine natural products (C. Bailly, Curr. Med. Chem.-Anti-Cancer Agents, 2004, 4, 363). We are investigating a related and unprecedented approach in which the halogens reside on the pyrrole ring. Synthesis of pyrrole precursors, development of cross-coupling conditions, and progress toward lamellarin analogs will be reported.