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Date Permissions Signed

5-7-2014

Date of Award

2014

Document Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Vyvyan, James R.

Third Advisor

Young, Jeff C. (Jeffery C.)

Abstract

The archazolids are a complex family of natural products with distinct structural features. Inspired by these unique structural characteristics, our group sought to synthesize an analogue of this family, dihydroarchazolid B. We were encouraged to synthesize this analogue due to its high potential to be a potent cytotoxic agent against the vacuolar-type ATPases (V-ATPases) and because it is a simpler analogue than the parent natural products from a synthetic perspective. Within this work, a ring-closing metathesis (RCM) approach was explored in depth towards the completion of our target. From these efforts, a metathesis deactivating stereotriad was uncovered in a key fragment needed for ring closure. Using the knowledge uncovered in our synthetic endeavors, a possible relay-ring closure event is discussed. The synthetic utility of exploring the effects of contiguous remote functionality on alkene reactivity is also demonstrated as knowledge of this type will better inform our future synthetic challenges.

Type

Text

DOI

https://doi.org/10.25710/836v-2x31

Publisher

Western Washington University

OCLC Number

879486682

Subject – LCSH

Macrolide antibiotics--Synthesis; Antineoplastic agents--Synthesis; Adenosine triphosphatase; Metathesis (Chemistry)

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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