Synthesis of unnatural analogues of narciclasine: Chemoenzymatic synthesis of 2-epi-1-hydroxymethylnarciclasine

An approach to the synthesis of novel C-1 analogues of narciclasine has been developed. The synthesis relies on chemoenzymatic dihydroxylation of an arene, Stille coupling, and an intramolecular Heck reaction to affect key transformations. The synthesis of the targeted C-1 analogues addresses a gap in literature where few narciclasine analogues have been prepared, with no C-1 homologues existing to date. The synthetic route to 2-epi-1-hydroxymethylnarciclasine, as well as a possible route to several other derivatives, is described in detail. Experimental and spectral data are provided for all newly synthesized compounds.

Name thesis:degree_name

Ph.D. Chemistry

Level thesis:degree_level

Doctoral

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

• Bedard, Korey

• Synthesis
• Natural products
• Amaryllidaceae
• Biocatalysis
• Anti-cancer

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/16873

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/16873