Xenitorin A, a member of the xenitorin family of compounds isolated in 2002, demonstrated potent cytotoxicity against A549 (lung) cancer cells with an ED<sub>50</sub> of 0.79 mg/mL. Our work aims to develop a viable synthesis of this natural product in order to better understand its biochemical mechanism of action and potentially improve its potency as an anti-lung cancer agent. We believe through the utilization of cysteine based catalysis, we can develop a catalytic, asymmetric Rauhut-Currier/Aldol condensation reaction which would provide the necessary bicyclic framework for the eventual synthesis of xenitorin A. The development of this methodology would provide the chemical community with a new procedure for the synthesis of enantio-enriched bicyclic products. Explorations into this methodology may also help to refute or support previously proposed mechanistic models of this and similar Rauhut-Currier transformations. This talk outlines our efforts to successfully prepare the acyclic precursor and initial studies of the proposed reaction. The talk will also include a discussion of the theoretical basis for the enantio/diastereoselectivity of our proposed reaction. Proposed synthetic steps following a successful Rauhut-Currier/Aldol Condensation to access xenitorin A will also be discussed.

Methodological study of a proposed, asymmetric Rauhut-Currier reaction/aldol condensation and current efforts to synthesize the anticancer agent xenitorin A

249th National Meeting (2015)

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