The vast majority of theses in this collection are open access and freely available. There are a small number of theses that have access restricted to the WWU campus. For off-campus access to a thesis labeled "Campus Only Access," please log in here with your WWU universal ID, or talk to your librarian about requesting the restricted thesis through interlibrary loan.

Date Permissions Signed


Date of Award


Document Type

Masters Thesis

Degree Name

Master of Science (MS)



First Advisor

Vyvyan, James R.

Second Advisor

O'Neil, Gregory (Gregory W.)

Third Advisor

Raymond, Elizabeth A.


The heliannuols are a family of allelochemicals that have been isolated from the common sunflower (Helianthus annuus). The 8-membered cyclic ether moiety found in many of the heliannuols is a rare motif in nature and provides a challenging synthetic target. It has been found that conformational constraint in the form of a Z olefin helps promote the cyclization of aryl epoxides to the 8-membered cyclic ether. Hiyama couplings of aryl iodides and cyclic vinyl siloxanes produce Z-styrenes in good to excellent yields. Due to the expense of the catalyst used for the synthesis of the siloxanes, an alternate pathway to the Z olefins utilizing vinyl cyclic boronic half acids was also pursued, but was ultimately unsuccessful. Due to the success of Hiyama couplings, the synthesis of glandulone B was pursued. The dimethoxyhydroquinone derivative of glandulone B was synthesized from an aryl iodide and cyclic vinyl siloxane in a 23% yield over 4 steps. Oxidation of the dimethoxyhydroquinone to glandulone B was explored.




Natural products--Synthesis, Sunflowers, Allelopathic agents--Synthesis


Western Washington University

OCLC Number



masters theses




Copying of this thesis 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.

Included in

Chemistry Commons