Synthetic routes to the madne natural products phakellin and palau'amine will be discussed. Both natural products consist of complex and unique frameworks that will require novel chemical transformations in order :o be successfully created. The inherient nucleophilicity of 2-aminoimidazole will be exploited in several key steps towards both natural products. Initially, synthetic efforts will be directed towards phakellin whose tetracyclic structure can be found in palau'amine as well. Important transformations include an intramolecular cyclization of a 2-aminoimidazole derivative with a tethered aldehyde, followed by trapping of the ntermediate with a pyrrole nitrogen. Once the structure of phakellin has been successfully completed, the /aluable information gained can then be applied to a synthesis of palau'amine. In addition to the reaction :lescdbed above, the nucleophUicity of 2-aminoimidazole will be used in an intermolecular addition with an aldehyde in the route towards palau'amine. This reaction will be followed by a series of intermolecular and ntramolecular substitutions that also take advantage of the nucleophilicity of 2-aminoimidazole. The result of :hese important trasformations would be the hexacyclic structure of palau'amine.
