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- Title
Enantioselective Organocatalytic Michael/Aldol Sequence: Anticancer Natural Product (+)- trans-Dihydrolycoricidine.
- Authors
McNulty, James; Zepeda‐Velázquez, Carlos
- 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.
- Subjects
ALDOLS; ANTINEOPLASTIC agents; NATURAL products; CHEMICAL synthesis; CHEMICAL precursors; AMINES; CHEMICAL reactions
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 32, p8450
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201403065