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Date of Award

Spring 2023

Document Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Vyvyan, James R.

Second Advisor

Murphy, Amanda R.

Third Advisor

Emory, Steven R.

Abstract

Natural products are an important class of molecules utilized in traditional medicine and inspire drug design in medicinal chemistry. Cananga odorata, a tree commonly known as ylang-ylang, contains natural products known to positively benefit health, and specifically promote liver health. One alkaloid isolated from Cananga odorata, cananodine, possesses cytotoxic properties, specifically against hepatocellular carcinoma (HCC). HCC is the most common type of liver cancer, with one million diagnoses projected by 2025 globally. Cananodine is a member of the guaipyridine alkaloid family, a class of compounds that feature a substituted pyridine bonded to a seven-membered ring. The first enantiomer of interest, (+)-cananodine, has demonstrated greater activity against HCC compared to the second target, (-)-cananodine. The molecule’s activity likely depends on its stereochemistry, so this efficient, enantioselective synthesis is critical since previous attempts yielded little product or lacked selectivity. In this study, the first proposed synthesis utilizes a modern enantioselective Heck reaction. The second unique route features a diastereoselective Evans alkylation that yields both (+)- and (-)-cananodine enantiomers. The selective synthesis of these small but intricate molecules makes progress in the development of new compounds that could improve the treatment of HCC.

Type

Text

Keywords

sesquiterpene, alkaloids, guaipyridine, cananodine, stereoselective, rupestine

Publisher

Western Washington University

OCLC Number

1380912063

Subject – LCSH

Sesquiterpenes; Alkaloids; Stereochemistry; Liver--Cancer--Treatment

Format

application/pdf

Genre/Form

masters theses

Language

English

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

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