Abstract
Enediyne natural products are known to inhibit the development of a neoplasm (cancer cell). Synthetic enediynes continue to be developed in laboratory to study their structure reactivity properties in an effort to develop more efficient drug candidates. The key event responsible for the biological properties is Bergman Cyclization of the enediyne unit to produce an aromatic diradical. These diradical then abstract hydrogen atoms from the DNA backbone in a tumor cell leading to apoptosis. Although enediynes may inhibit the development of neoplasm, they lack the selectivity to specifically target tumor cells. This project examines the incorporation of methoxy groups conjugated to the enediyne to improve photochemical activation towards Bergman cyclization. The methoxy groups are composed of an electron donating oxygen containing a methyl group that is attached to the enediyne core as a substituent. This project will examine the synthesis and photo-reactivity to better understand factors controlling light activated Bergman Cyclization. Overall, photoactivation may provide selective activation by delivery of light while electronic effects from the methoxy groups can increase reaction yield and reduce reaction time to help develop more efficient enediyne pro-drugs. The goal of this project is to study the methoxy effect at different locations within the enediyne structure.