Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes
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Title |
Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes
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Creator |
AYYAGARI, N
JOSE, D MOBIN, SM NAMBOOTHIRI, INN |
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Subject |
DOUBLE MICHAEL REACTION
FEIST-BENARY REACTION ORGANOCASCADE REACTIONS BIFUNCTIONAL THIOUREA CONJUGATE ADDITION ANALOGS WATER DERIVATIVES CANCER DIASTEREOSELECTIVITY Curcumin Nitroalkene Double Michael addition Feist-Benary reaction |
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Description |
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.
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Publisher |
PERGAMON-ELSEVIER SCIENCE LTD
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Date |
2012-06-26T08:40:40Z
2012-06-26T08:40:40Z 2011 |
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Type |
Article
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Identifier |
TETRAHEDRON LETTERS,52(2)258-262
0040-4039 http://dx.doi.org/10.1016/j.tetlet.2010.11.017 http://dspace.library.iitb.ac.in/jspui/handle/100/14206 |
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Language |
English
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