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Enantioselective Organocatalytic Michael/Aldol Sequence: Anticancer Natural Product (+)‐ trans ‐Dihydrolycoricidine
Author(s) -
McNulty James,
ZepedaVelázquez Carlos
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403065
Subject(s) - stereocenter , enantioselective synthesis , aldol reaction , michael reaction , natural product , chemistry , intramolecular force , stereochemistry , sequence (biology) , cinnamaldehyde , total synthesis , amine gas treating , organocatalysis , organic chemistry , catalysis , biochemistry
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.