Dr. Gregory O'Neil Dr. Gregory O'NeilAssistant Professor
Department of Chemistry
Western Washington University
Grant 49499-UNI1
Metathesis Reactions of Acyloxysulfones for Polyene Synthesis

Dr. Gregory W. O'Neil is an Assistant Professor at Western Washington University whose research interests include the synthesis of natural products; asymmetric synthesis and catalysis; and organometallic chemistry. He has received PRF funding for research focusing on metathesis reactions for polyene synthesis.

Prior success has been achieved in the areas of organic and polymer synthesis through olefin metathesis. Here, building block chemicals (e.g., ethylene) are catalyzed and change structure to form a variety of compounds for use in, for example, pharmaceutical drug production, materials manufacturing, etc.

Traditional methods of metathesis prove less successful, though, in applications involving polyene syntheses (systems with more than one alkene). Dr. O'Neil and his group have discovered a promising and new method that allows for access to polyene subunits—and subsequent synthesis—through the introduction of β-acyloxysulfones. The process has made it possible for the team to side-step difficulties typically associated with chemoselectivity by creating a metathesis reaction and reductive elimination sequence to produce certain diene and triene fragments. Examples include conjugated, 1,6-, and 1,7-dienes that are difficult to prepare by standard methods.

Dr. O'Neil and his team have applied their method to the synthesis of several natural product targets including a class of algal lipids known as long-chain alkenones. This application is of particular interest, because algae have been identified as a potential source for biofuels. Further research will focus on applying the method to varied and more complex systems.

Dr. O'Neil's interest in this research goes back at least four years, when he was inspired by his doctoral research on the synthesis of the spirastrellolide natural products. Since then, his research has gone from more fundamental and theoretical to applied. Moving forward, he intends to investigate a novel synthesis for conducting polymers for application to solar energy efforts.

PRF awarded Dr. O'Neil a two-year Undergraduate New Investigator Grant, with a one-year extension. Dr. O'Neil is grateful for the significant contribution of this funding to providing equipment, supplies, and support for his team of undergraduate students.

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Dr. Ridgway
Polyene Synthesis
Dr. O'Neil
Dr. Bali
Faults and Fluid Flow
Dr. Huntington