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Date Permissions Signed


Date of Award

Winter 2016

Document Type

Masters Thesis

Degree Name

Master of Science (MS)



First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Murphy, Amanda R.

Third Advisor

Bussell, Mark E.


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.




Sulfones, Alkenes--Synthesis, Lactones--Synthesis, Heterocyclic compounds--Synthesis, Ring formation (Chemistry), Metathesis (Chemistry), Chemistry, Organic


Western Washington University

OCLC Number



masters theses




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