Efforts toward the total synthesis of apoptolidin C: A catalytic, asymmetric approach

ORGN 703

James S. Hale, jsh30@pitt.edu and Scott G Nelson, sgnelson+@pitt.edu. Department of Chemistry, University of Pittsburgh, 219 Parkman Ave., Pittsburgh, PA 15260
The total synthesis of apoptolidin C, a highly selective and cytotoxic polypropionate macrolide, is currently under investigation in our laboratory. The highlights of our synthetic strategy include catalytic, asymmetric formation of multiple stereocenters via the acyl halide-aldehyde cyclocondensation (AAC). We have successfully integrated the AAC technology into a highly efficient route to the aglycone core of apoptolidin C. This presentation will focus on the work towards the completion of the C1-C11 synthon including an assessment of various strategies for its construction.