Combretastatin A-4, a naturally occurring compound, isolated from the South African bush willow Combretum Caffrum, has analogs such as chalcones, which have antibacterial, anti mitotic, anticancer, and antibiotic properties. Here, the chalcones are the basis for the synthesis of pyrroles. Lamellarin pyrroles have been sythesised from chalcones using electroncyclization chemistry of chalcones with glycine esters. The focus here is to generate pyrroles from chalcones en route to to ynedienes. Ynedienes can be generated by the coupling of a halopyrrole with a terminal alkyne. These ynedienes will be examined for their ability to induce DNA cleavage, via diradicals following the ynediene cyclization. The synthesis and purification of an O-protected hydroxyl chalcone has proven to be challenging. The scope of chalcones that can be utilized in the electrocyclization process has been expanded and will be discussed. Use of N-iodosuccinimide in the reaction process, provides a halo-substituted pyrrole that will be coupled with terminal alkynes. They alkyne provides handle for versatility in the next step(s). Its use as a handle towards a variety of analogs will be discussed.
