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Master of Science (MS)
O'Neil, Gregory (Gregory W.)
Murphy, Amanda R.
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
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Phan, Iris T., "Ring-Closing Metathesis Reactions of Acyloxysulfones: Synthesis of γ-Alkylidene Butenolides" (2016). WWU Graduate School Collection. 470.