Date of Completion

2019

Document Type

Honors College Thesis

Department

Chemistry

Type of Thesis

Honors College

First Advisor

Dr. Matthias Brewer

Keywords

organic synthesis, drug development, lithiation, cancer, natural products synthesis, aromatic substitution

Abstract

Fusarochromanone is a powerful anticancer mycotoxin exhibiting unique molecular structure and biological activity. Fusarochromanone is produced by rare strains of fusarium equiseti and is not readily accessible for study from its natural source; thus, an efficient laboratory synthesis practical for large-scale production is an attractive goal. Previously reported syntheses of Fusarochromanone are limited by prohibitively expensive starting materials and low-yielding key steps. In this work, novel approaches to Fusarochromanone synthesis using directed ortho- metalation strategies have been proposed and tested. A cost-effective, scalable synthesis of Fusarochromanone has been achieved, and groundwork has been laid that will direct future efforts to improve the developed synthesis.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

Available for download on Sunday, May 16, 2021

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