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Date Permissions Signed
3-29-2016
Date of Award
Winter 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
Bussell, Mark E.
Abstract
As we set out to investigate ring-closing methatesis reactions of acyloxysulfones, we discovered that treatment with triethylamine resulted in its quantitative conversion into the γ-alkylidene butenolides. γ-Alkylidene Butenolides are common to a number of biologically important natural products, and have been of great interest. To date, there has been no metathesis-based synthesis of γ-alkylidene butenolides making our approach the first. Development of the metathesis-based approach has allowed us to synthesize a variety of γ-alkylidene butenolides from the RCM products in high yields (69-100%). The elimination is proposed to proceed via an E1cb mechanism leading to (Z)-γ-alkylidene butenolides as the major products. In an attempt to showcase this method in the context of complex γ-alkylidene butenolide natural products, we successfully synthesized two model spirocyclic butenolides (5,5- and 6,5-). The synthesis of the model compounds will lead us one step closer in achieving the total synthesis of a natural spiro-butenolide product.
Type
Text
DOI
https://doi.org/10.25710/vjrq-ar63
Publisher
Western Washington University
OCLC Number
944187788
Subject – LCSH
Sulfones; Alkenes--Synthesis; Lactones--Synthesis; Heterocyclic compounds--Synthesis; Ring formation (Chemistry); Metathesis (Chemistry); Chemistry, Organic
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.
Recommended Citation
Phan, Iris T., "Ring-Closing Metathesis Reactions of Acyloxysulfones: Synthesis of γ-Alkylidene Butenolides" (2016). WWU Graduate School Collection. 470.
https://cedar.wwu.edu/wwuet/470