Application of Mn(III) Oxidative Cyclizations to Natural Product Synthesis

This work begins with a brief review of manganese(III) acetate free radical oxidative cyclization chemistry and its application toward functionalizing nitrogen containing heterocycles. Exploration of a cyclopropane ring opening reaction using indoline, and subsequent manganese(III) cyclization chemistry will be presented as a possible route towards a family of natural products called the flinderoles. Work on the construction of the core of several indole alkaloids from the genus Tabernaemontana, including tronocarpine, chippiine, and dippinine B, will be explored with utilization of manganese(III) cyclizations. Hopes of accessing an advanced common intermediate for each of these natural products will be discussed due to structural similarities that converge nicely with the use of manganese(III) as a key synthetic step.

Name thesis:degree_name

M Sc

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher

The University of Western Ontario

Year dc:date.issued

2014

Author dc:creator

• Landschoot, Bryan

Advisor dc:contributor.advisor

• Michael A. Kerr

• Manganese(III) Acetate
• Natural Product Synthesis
• Flinderole
• Tronocarpine
• Oxidative Radical Cyclization
• Chippiine

Language dc:language.iso

en_ca

Handle dc:identifier.uri

https://hdl.handle.net/20.500.14721/35108

OAI identifier oai:identifier

oai:uwo.scholaris.ca:20.500.14721/35108