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SYNTHESIS OF UNSYMMETRICAL TETRA(AMINOMETHYL)ADAMANTANE AMIDES
Iris Cruz, Asmik Oganesyan, and Carlos Gutierrez*
Department of Chemistry and Biochemistry,   California State University, Los Angeles 90032

Although iron is the fourth most abundant element it is highly insoluble under cellular conditions.  A bacterium utilizes siderophores to increase the solubility of iron.  These siderophores enter bacteria through highly selective receptors.  The siderophore of interest is enterobactin (1), which enters through the FepA receptor.   In order to further study the entrance of the siderophore, we synthesize a bifunctional enterobactin-analogue.  This unsymmetric analogue demands the development of new chemistry; here we present synthesis of tricatecholateadamantane (2) protected intermediate starting from inexpensive adamantane.