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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/14206

Title: Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes
Authors: AYYAGARI, N
JOSE, D
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: DOUBLE MICHAEL REACTION
FEIST-BENARY REACTION
ORGANOCASCADE REACTIONS
BIFUNCTIONAL THIOUREA
CONJUGATE ADDITION
ANALOGS
WATER
DERIVATIVES
CANCER
DIASTEREOSELECTIVITY
Issue Date: 2011
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Citation: TETRAHEDRON LETTERS,52(2)258-262
Abstract: The reaction of curcumins with nitroalkenes has been investigated for the first time. Highly functionalized cyclohexanones possessing three contiguous chiral centers with complete diastereoselectivity have been synthesized through an inter-intramolecular double Michael reaction involving curcumin and nitroalkene under extremely simple experimental conditions (K(2)CO(3) in aqueous THF). Under identical conditions, curcumins react with alpha-bromonitroalkenes to afford dihydrofurans through an intermolecular Michael addition-intramolecular nucleophilic substitution (O-alkylation), which is analogous to an 'interrupted' Feist-Benary reaction. These novel transformations of curcumins empower us to expand the repertoire of curcumin based therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.
URI: http://dx.doi.org/10.1016/j.tetlet.2010.11.017
http://dspace.library.iitb.ac.in/jspui/handle/100/14206
ISSN: 0040-4039
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