Methodology developed during the synthesis of a truncated analog of hydramycin

Several unique strategies were developed and employed in the synthesis of 2-(1,2-dihydroxy-1-oxiranylethyl)-5-methylchromen-4-one (1) during a model study for the synthesis of hydramycin (2)-an antitumor antibiotic. Hydramycin, a pyranoanthraquinone, was isolated from a strain of Streptomyces and shown to exhibit both cytotoxic and antibiotic properties. This dissertation will cover the developments, challenges and solutions discovered in the total synthesis of truncated analog 1, which contains the functionality found in 2, and the methodology to generate an anthraquinone system that could be used for the ultimate synthesis of 2.