The proposed research will develop the cycloaddition of the isoquinolinium salts as a method for the synthesis of two classes of anthracyclines with antitumor and anti HIV activity. One class, the sakiomysins and related compounds are characterized by their angular framework which is highly oxidized. Sakiomycin A has been shown to inhibit the proliferation of HIV (AIDS) virus, presumably by inhibition of reverse transcriptose. The second class, the C-glycoside analogs of the clinically important anthracyclines, are not available in nature. The biological activity of the C-glycosides will provide important information about the requirements for cytotoxicity and cardiotoxicity of the parent compounds.