Development and application of a borylative heck reaction and towards the total synthesis of nimbolide
Ryffel, Peter
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https://hdl.handle.net/2142/122053
Description
Title
Development and application of a borylative heck reaction and towards the total synthesis of nimbolide
Author(s)
Ryffel, Peter
Issue Date
2023-12-05
Director of Research (if dissertation) or Advisor (if thesis)
Sarlah, David
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(s)
Borylative Heck
Total Synthesis
Methodology
Abstract
A borylative Heck reaction was developed that allowed for the facile construction of a variety of bicyclic cores that are central to the structures of terpene natural products. It was discovered that bidentate phosphine mono-oxide ligands were critical to not only the product selectivity of this reaction, but also the diastereoselectivity. Additionally, the reaction was demonstrated in synthetic studies that are currently on going. Finally, a different variant of this borylative Heck reaction that utilized a more oxidized vinyl iodide was developed and is currently being utilized in a synthetic route towards the natural product nimbolide, which has potential as an anti-cancer drug.
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