Efforts toward the total synthesis of apoptolidin C via an iterative application of the acyl halide-aldehyde cyclocondensation

ORGN 702

Thomas R Vargo and Scott G Nelson, sgnelson+@pitt.edu. Department of Chemistry, University of Pittsburgh, 219 Parkman Ave., Pittsburgh, PA 15260
The synthesis of the biologically active polypropionate macrolide apoptolidin C is currently under investigation. This synthesis highlights a catalytic asymmetric approach to structurally complex polypropionate arrays based on our acyl halide-aldehyde cyclocondensation (AAC) reaction. Employing the AAC technology using cinchona alkaloid derived catalysts, we have successfully demonstrated a catalytic and asymmetric synthesis of the aglycone core of apoptolidin C. This presentation describes the synthesis of the C12-C28 synthon, starting from the readily available methoxy acetaldehyde and completion of the aglycone core.