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The verticillins, a class of epipolythiodioxopiperazine alkaloids (ETP) have gained attention due to their potent activity against cancer cells, noted both in vitro and in vivo. In this study, ester, carbonate, sulfonate and carbamate derivatives were synthesized using the isolated natural products from Clonostachys rogersiana. Semi-synthetic efforts were designed to explore the reactivity of the C11 and C11' hydroxy substituents. Verticillin H was used as a starting material to generate nine semisynthetic analogues. Likewise, verticillin A succinate was synthesized as a way of proving the successful application of these reactions on various ETP starting materials. The skills of synthetic chemistry to generate analogues were coupled with those of natural products chemistry to both monitor reaction progress (i.e., ¹H NMR) and purify leads (i.e., prep-HPLC). The synthesized compounds and their corresponding starting materials were screened for activity against a panel of breast and ovarian cancer cell lines: MDA-MB-435, MDA-MB-231, and OVCAR3.

Joanna Burdette

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