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Regiospecific synthesis of arenofurans via cascade reactions of arenols with Morita-Baylis-Hillman acetates of nitroalkenes and total synthesis of isoparvifuran

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Title Regiospecific synthesis of arenofurans via cascade reactions of arenols with Morita-Baylis-Hillman acetates of nitroalkenes and total synthesis of isoparvifuran
 
Creator KUMAR, T
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject Arenofurans
Isoparvifuran
Nitroalkenes
Morita-Baylis-Hillman acetates
Cascade reaction
SOLVENT-FREE CONDITIONS
C-BOND FORMATION
ALLENYL KETONES
CONJUGATED NITROALKENES
POLYSUBSTITUTED FURANS
3,4-SUBSTITUTED FURANS
ANTIMICROBIAL ACTIVITY
EFFICIENT SYNTHESIS
FACILE SYNTHESIS
BENZOFURANS
 
Description A cascade process involving an S(N)2' reaction and an intramolecular oxa-Michael addition has been developed by treating Morita-Baylis-Hillman acetates of nitroalkenes with arenols, such as beta-naphthols, alpha-naphthols, and substituted phenols under basic conditions. The products, arenofurans, are formed as single regioisomers in good to excellent yield in most cases. The methodology has been successfully employed for the total synthesis of an anti fungal agent isoparvifuran. (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T05:33:05Z
2014-10-16T05:33:05Z
2013
 
Type Article
 
Identifier TETRAHEDRON, 69(24)4964-4972
http://dx.doi.org/10.1016/j.tet.2013.04.023
http://dspace.library.iitb.ac.in/jspui/handle/100/15346
 
Language en