University of Arkansas, Fayetteville


Iron complex chemistry that opens a new door to the medicinal and pharmaceutical worlds is the aim of this research. Specifically, ortho-quinone methide moieties are intermediates in several antitumor drugs and have been identified as bioreductive alkylators of DNA. In our research, a class of iron compounds has been targeted to resemble these quinone methides. It is hoped that these new compounds could be modified to provide a window of opportunity toward the discovery of a selective mode of drug delivery. We have focused our efforts on generating a reactive transition metal complexed 5-membered ring analog of o-quinone methide based on our earlier reports of CpFe(CO)2 (butadienyl) complexes. In this vein, we have elaborated this chemistry by preparing and reacting a lithionaphthalene allene with CpFe(CO)2I. which gave the desired naphthalene annulated sigma complex. This complex thermally rearranged to the desired naphthalene annulated 5-membered ring quinone methide analog. Upon photolysis, this complex successfully mimicked its antecedent and alkylated alcohols. Thus, we here report our initial study of the preparation and chemistry of a transition metal complexed 5-membered ring quinone methide analog. Its reactions with alcohols have accomplished the first step toward the ultimate goal of selectively alkylating DNA.