Development and application of a borylative heck reaction and towards the total synthesis of nimbolide

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.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2023

Author dc:creator

• Ryffel, Peter

Contributors dc:contributor

• Sarlah, David

• Borylative Heck
• Total Synthesis
• Methodology

Statement dc:rights

• Copyright 2023 Peter Ryffel

Language dc:language

en, eng

Handle dc:identifier

https://hdl.handle.net/2142/122053

OAI record oai:identifier

https://www.ideals.illinois.edu/oai-pmh?verb=GetRecord&metadataPrefix=etdms&identifier=oai%3Awww.ideals.illinois.edu%3A2142%2F122053