Publication Date

5-23-2013

Advisor(s)

Michael Calter

Major

Chemistry

Language

English (United States)

Abstract

Antifungal 8, which lacks a common name, has a core structure similar to GlaxoSmithKline's griseofulvin, a potent antifungal agent, and is able to treat various systemic fungal infections in humans with compromised immune systems, livestock, and even plants. Antifungal 8 has been previously synthesized through a stereochemically uncontrollable, photochemical intramolecular ring-forming reaction of a benzophenone derivative. The asymmetric total synthesis of antifungal Compound 8 involves using an organocatalyzed asymmetric reaction, "Interrupted" Feist-Benary reaction to induce chirality and preferentially yield one enantiomer of antifungal 8. Asymmetric total synthesis, which is attempted herein, of both enantiomers of antifungal 8 separately permits identification of the enantiomer with the stronger antifungal properties.

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