Presentation Title

Synthesis of Furanolactone Cores via Ketyl Radical Cyclization Using a Ruthenium Catalyst

Faculty Mentor

Jeffrey Cannon

Start Date

18-11-2017 12:30 PM

End Date

18-11-2017 1:30 PM

Location

BSC-Ursa Minor 145

Session

Poster 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

The furanolactone motif is prevalent in a large number of natural products with many potential medicinal applications. We have developed a methodology to rapidly synthesize furanolactone the furanolactone motif from cheap, readily available starting materials. Our process utilizes a photoactivated ruthenium catalyst, a Lewis Acid, and is carried out in mild conditions under blue LEDs. Our work thus far has focused on optimizing our reaction conditions and broadening the scope of substrates that our methodology applies to. The current reaction results in significant amounts of a single-furan ring product, which can be either an anti or syn diastereomer. In order to reach our desired furanolactone product, a step to epimerize the anti diastereomer and lactonize the syn diastereomer is needed. Much of our recent work has focused on a development and optimization of this epimerization step, which utilizes only a Lewis acid and has shown high yields. We have proven that our methodology is applicable to a variety of substrates, and in the future hope to use this process to synthesize natural products containing the furanolactone motif.

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Nov 18th, 12:30 PM Nov 18th, 1:30 PM

Synthesis of Furanolactone Cores via Ketyl Radical Cyclization Using a Ruthenium Catalyst

BSC-Ursa Minor 145

The furanolactone motif is prevalent in a large number of natural products with many potential medicinal applications. We have developed a methodology to rapidly synthesize furanolactone the furanolactone motif from cheap, readily available starting materials. Our process utilizes a photoactivated ruthenium catalyst, a Lewis Acid, and is carried out in mild conditions under blue LEDs. Our work thus far has focused on optimizing our reaction conditions and broadening the scope of substrates that our methodology applies to. The current reaction results in significant amounts of a single-furan ring product, which can be either an anti or syn diastereomer. In order to reach our desired furanolactone product, a step to epimerize the anti diastereomer and lactonize the syn diastereomer is needed. Much of our recent work has focused on a development and optimization of this epimerization step, which utilizes only a Lewis acid and has shown high yields. We have proven that our methodology is applicable to a variety of substrates, and in the future hope to use this process to synthesize natural products containing the furanolactone motif.