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Lewis acid promoted C-C and copper-catalyzed C-O bond formation: Synthesis of neoflavans
B. Suchand, J. Krishna, K. Mritunjoy,
Published in Royal Society of Chemistry
2014
Volume: 4
   
Issue: 27
Pages: 13941 - 13945
Abstract
An intramolecular [Cu]-catalyzed C-O bond formation for the synthesis of neoflavans is presented. Lewis acid promoted Friedel-Crafts Michael addition of electron rich aromatic systems onto the double bond of the cinnamate ester was employed to furnish a β-diaryl ester. Electrophilic aromatic bromination of the β-diaryl ester and reduction/Grignard addition furnished the required precursor alcohols. The method is applicable to the synthesis of neoflavans containing tertiary as well as quaternary carbon centers. Significantly, the neoflavan substructures are present in biologically active compounds. © 2014 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetRSC Advances
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN20462069