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Updated: Apr 27, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Enantioselective organocatalytic Michael/aldol sequence: anticancer natural product (+)-trans-dihydrolycoricidine
James McNulty1, Carlos Zepeda-Velázquez
1Department of Chemistry and Chemical-Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 (Canada) //www.chemistry.mcmaster.ca/mcnulty/index.html. jmcnult@mcmaster.ca.
Abstract:
A total synthesis of the anticancer natural product (+)-trans-dihydrolycoricidine is reported from α-azidoacetone and cinnamaldehyde precursors. Key elements include an asymmetric organocatalytic sequence proceeding by a regiospecific secondary-amine-catalyzed syn Michael addition followed by an intramolecular aldol reaction. The sequence results in the formation of an advanced intermediate, containing three stereogenic centers, in one step which and was converted into the title compound in eight steps.
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