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Date Permissions Signed

5-13-2016

Date of Award

Spring 2016

Document Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Murphy, Amanda R.

Third Advisor

Antos, John M.

Abstract

We have developed a new samarium diiodide-mediated elimination/isomerization reaction of benzoyl esters, capable of delivering olefinic products with high yield and selectivity depending on substrate structure and the additives used. The ability to selectively synthesize terminal, non-conjugated alkene substituents inspired us to use these optimized conditions in order to complete the total synthesis of the natural product, honokiol. Honokiol is a biaryl natural product isolated from magnolia trees that displays desirable oncological properties as evidenced by several biological studies in recent years. We found that our initially proposed pathway for completing the synthesis of honokiol was not a feasible route due to the sensitivity of the allylic groups. However, after adjusting our synthetic route, we were able to complete the synthesis of honokiol in 40% overall yield.

Type

Text

DOI

https://doi.org/10.25710/30yh-hj12

Publisher

Western Washington University

OCLC Number

949905132

Subject – LCSH

Samarium--Isotopes; Honokiol--Synthesis; Biphenyl compounds--Synthesis; Lignans--Synthesis

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 thesis for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.

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