Campus Access Only

All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.

Date of Award


Document Type


Degree Name

Doctor of Philosophy (Ph.D.)


Graduate School

First Advisor

Paul H. Gross

First Committee Member

Charles A. Matuszak

Second Committee Member

Herschel Frye

Third Committee Member

Michael Minch

Fourth Committee Member

David Fries


The decision to attempt the synthesis of furo [3, 2-b] furan was based on four considerations. Firstly, there are an abundance of synthetic and naturally occurring compounds, especially carbohydrate derivatives, containing this ring system in a partially or fully saturated state. Secondly, some of these compounds are physiologically active and others are important industrially. Thirdly, no compound, synthetic or naturally occuring, containing the fully unsaturated nucleus has been reported. Yet this molecule has an uninterrupted chain of six carbon atoms and may conceivably be formed from certain hexose derivatives. By analogy with compounds containing the saturated ring, furo[3,2-b] furan may be physiologically active. Lastly, there is only one synthetic 3-alkoxyfuran, 3·-methoxyfuran. Any intermediate successes toward the stated goal as well as achievement of the final objective will expand knowledge in the difficult area of 3-substituted furan synthesis especially in the presently unexamined area of 3-alkoxyfuran synthesis.