Investigation into a one-pot synthesis of phenanthrene

CHED 589

Samantha C Chesak and Scott T Handy, shandy@mtsu.edu. Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132
As part of an ongoing project directed at performing polycoupling reactions on polyhaloaromatics, we have investigated the sequential, one-pot Sonogashira and Suzuki couplings of 1,2-dihalobenzenes. The resulting alkynylated diaryls can then be closed in a subsequent step to afford phenanthrenes in a very concise fashion. This two step approach to functionalized phenanthrenes will be among the most concise reported to date. Further, while many uses of these phenanthrenes can be envisioned, the current target is colchicine, a naturally occurring alkaloid with several therapeutic uses.