Total synthesis of quinoline-5,8-dione analogs and 7-N-Butyryldemethyllavendamycin benzyl ester : an honors thesis [(HONRS 499)]/ by Darric E. Baty.
The synthesis of 7-butyramidoquinoline-5,8-dione-2-carboxylic acid, pyrrolidine 7butyramidoquinoline-5,8-dione-2-carboxamide, and 7-N-butyryldemethyllavendamycin benzyl ester are reported. The carboxylic acid was synthesized from the commercially available 8hydroxy-2-methylquinoline via nitration, reduction-butyrylation, oxidation to the dione and then to an intermediate aldehyde, followed by final oxidation to the product. Reaction of the acid with N-hydroxysuccinimide and then pyrrolidine afforded the ester. The lavendamycin analog was synthesized by condensation of the intermediate aldehyde and a tryptophan derivative. These three compounds can now be tested for biological activity. This will hopefully aid in the current structure-activity relationship studies being performed on the related quinones and lavendamycin analogs synthesized as chemotherapeutic agents.