The kinamycins and lomaiviticins constitute a small family of bacterial metabolites that contain a diazo functional group embedded within a highly unsaturated carbocyclic skeleton (diazofluorene). Members of this family have demonstrated potent antimicrobial and antiproliferative activities, and evidence implicates DNA as a potential cellular target. The lomaiviticins in particular are highly complex and exceedingly unstable, and present several challenges and opportunities for chemical synthesis. This talk will focus on our laboratories' work in this area, beginning with our syntheses of kinamycin F and lomaiviticin aglycon, and progressing to studies aimed at elucidating the interaction of these metabolites with DNA.
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