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.
Means, T. (2002). Synthesis and Chemistry of Naphthalene Annulated Trienyl Iron Complexes: Potential Anticancer DNA Alkylation Reagents. Inquiry: The University of Arkansas Undergraduate Research Journal, 3(1). Retrieved from https://scholarworks.uark.edu/inquiry/vol3/iss1/18