The total synthesis of apoptolidin C (3), a highly selective cytotoxic macrolide, has been under investigation in our lab. Work completed includes the synthesis of the C1-C11 fragment 29, the macrocyclic core 3b, and the disaccharide subunit 31. These goals have been realized utilizing catalytic, asymmetric reaction methodology including the acyl halide-aldehyde cyclocondensation (AAC) and proline catalyzed dimerization of simple aldehyde starting materials 33-38. *Please refer to dissertation for diagrams. |