Date of Award

Spring 2026

Degree Type

Thesis

Department

College of Pharmacy

Director of Thesis

Juan Francisco Leon

Second Reader

Todd Romoff

Abstract

Cannabidiol (CBD) is a non-psychoactive phytocannabinoid derived from Cannabis Sativa with well-documented antioxidant and anti-inflammatory properties, yet its clinical utility is limited by moderate receptor selectivity, rapid hepatic metabolism, and broad pharmacological activity on the central nervous system (CNS). This thesis describes the design and partial execution of a multi-step synthetic route aimed at generating CBD/CBD-derived chalcone intermediates for potential therapeutic applications for neuroinflammation. The steps encompass an O-methylation, O-acetylation, and a Fries rearrangement. The first three steps were completed successfully and reproducibly shown through 1H-NMR and 12C-NMR; however, purification of the fourth step was not successful within the available timeframe. In parallel, all four steps of the CBN synthetic pathway were successfully yielded. These chalcone intermediates are intended to be a precursor to a collection of derivatives: CBD/CBN-flavones, CBD/CBN-benzodiazepines, and CBD/CBN-pyrazoles, which are all seen as “privileged scaffolds” in medicinal chemistry. The results establish a reproducible synthetic foundation that, once fully optimized, can support the systematic production of novel CBD- and CBN-based derivatives. Future work should prioritize completion of the Fries rearrangement step and purification in the CBD pathway, followed by pharmacological assays to evaluate the bioactivities of the resulting chalcone-derived compounds.

First Page

1

Last Page

42

Rights

© 2026, Josephine Mosser

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