Approaches Towards a Total Synthesis of Daphenylline

The following work describes the synthesis of advanced intermediates enroute to daphenylline. Construction of the ABCE tetracyclic skeleton of daphenylline was accomplished in thirteen steps with seven percent overall yield from commercially available (S)-carvone through [3,3]-allyl cyanate-to-isocyanate rearrangement, intramolecular Heck Reaction, and Intermolecular Diels-Alder/benzannulation strategies. Efforts towards the synthesis of daphenylline’s D ring are discussed. A terse introduction to the scientific literature of daphniphyllum alkaloids and a comprehensive overview of selected approaches and all previous syntheses of daphenylline is given. Experimental procedures and spectroscopic data are provided for all new compounds.

Name thesis:degree_name

M.Sc. Chemistry

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Department of Chemistry

Grantor

Brock University

Year dc:date.issued

2022

Author dc:creator

• Miskey, Scott

• Total Synthesis
• Natural Products
• Daphenylline
• Daphniphyllum Alkaloids
• Sigmatropic Rearrangement

Statement dc:rights

• Attribution-NonCommercial-NoDerivatives 4.0 International

Licence dc:rights.uri

• http://creativecommons.org/licenses/by-nc-nd/4.0/

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/17120

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/17120