Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions and application to the total synthesis of (-)-pironetin

ORGN 919

Scott G. Nelson, sgnelson@pitt.edu and Xiaoqiang Shen, xis7@pitt.edu. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260
A catalytic enantioselective total synthesis of naturally occurring anticancer product (-)-pironetin will be described. The synthesis is characterized by extensive use of reaction methodologies based on catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions. The synthesis also incorporates an iridium-catalyzed olefin isomerization.