Improved synthesis of the Lamellarins

ORGN 277

Scott T Handy, shandy@mtsu.edu, Department of Chemistry, Middle Tennessee State University, Box 68, Murfreesboro, TN 37132 and Yanan Zhang, yanan.zhang@binghamton.edu, Department of Chemistry, SUNY Binghamton, Binghamton, NY 13902.
During our total synthesis of lamellarins, a family of marine natural products, we have employed the sequential regiocontrolled halogenation/Suzuki coupling reaction approach. A highly efficient second-generation synthesis has been developed in our group based on the study of regioselective Suzuki couplings on polyhalopyrrole compounds. Regioselectivity can be predicted by 1H and 13C NMR chemical shift values of the parent non-halogenated compounds. And the order of the coupling can be controlled by the sequence of the addition of the boronic acids. By employing this one-pot polycoupling strategy, the synthetic pathway could be greatly shortened by up to 4 steps. Variations in conditions of improving the selectivity and applications of this method to the second-generation synthesis of lamellarins will be discussed.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Monday, 14 March 2005 Convention Center -- Room 10, Oral

Division of Organic Chemistry

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