Publication Date

April 2018

Advisor(s)

Michael Calter

Major

Chemistry

Language

English (United States)

Abstract

The employment of newly discovered, catalytic, asymmetric, carbon-carbon bond forming reactions can allow compounds with various functionalities to be synthesized. Specifically, an antifungal compound referred to as antifungal 8, can be produced by such a scheme. The racemate of this species has only been previously made through a photochemical reaction of a benzophenone.1 Even in its racemic form, antifungal 8 has displayed promising antifungal activity, rivaling that of its parent compound, griseofulvin.1 Griseofulvin is a common antifungal drug that has been rated one of the most essential medicines by the World Health Organization. Since the racemate of antifungal 8 possesses biological activity that surpasses that of griseofulvin against several fungal strains, an asymmetric synthesis of antifungal 8 is desirable. After all, the isolated enantiomer will possess twice the biological activity of the racemate.2 The suggested multistep route for the synthesis of antifungal 8 includes two of the major components that are characteristic of these modern asymmetric reactions: an ?Interrupted? Feist-Benary reaction and an aromatization step. First, the nucleophile for the ?Interrupted? Feist-Benary reaction is synthesized in several steps; these steps include a silylation reaction, acetal formation, a Grignard reaction, and a Dieckmann condensation. The nucleophile then reacts with the synthesized electrophile, prepared through tosyloxylation of an acetophenone; this yields the ?Interrupted? Feist-Benary product. Thereafter, the compound is aromatized, tosylated, and reduced. The species will then be chlorinated, the alkoxy group will be removed, the compound will undergo triflation, and it will be subjected to a double methylation. The successful synthesis of antifungal 8 by this method will not only generate a useful, biologically active compound, but will aid in the understanding of modern, catalytic, asymmetric, carbon-carbon bond forming reactions. These contemporary reactions will then be employed more widely to produce compounds with various biological functionalities, including anticancer, antibiotic, and antiviral agents.

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