Synthesis of unnatural analogues of narciclasine: Chemoenzymatic synthesis of 2-epi-1-hydroxymethylnarciclasine
type: CreativeWork
description: 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.
abstract: 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.
author: Bedard, Korey
language: eng
keywords: Synthesis, Natural products, Amaryllidaceae, Biocatalysis, Anti-cancer
date published: 2022-10-21T15:46:25Z
date modified: 2026-07-24T01:23:16Z
provider: Brock University
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: Brock University

PropertyValue
property ID: Handle
value: http://hdl.handle.net/10464/16873