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Benzofuran as a dienophile in pi(4)s+pi(2)s cycloaddition with cyclohexa-2,4-dienones. Studies on synthesis and photoreaction of dihydrobenzofuran annulated bicyclo[2.2.2]octenones

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Title Benzofuran as a dienophile in pi(4)s+pi(2)s cycloaddition with cyclohexa-2,4-dienones. Studies on synthesis and photoreaction of dihydrobenzofuran annulated bicyclo[2.2.2]octenones
 
Creator JARHAD, DB
BEHERA, TK
SINGH, V
 
Subject DIELS-ALDER REACTIONS
NATURAL-PRODUCT SYNTHESIS
ALPHA-HYDROXY KETONES
STEREOSELECTIVE ROUTE
PERIODATE OXIDATION
ORGANIC-SYNTHESIS
REARRANGEMENT
TANDEM
RING
STEREOCHEMISTRY
Diels-Alder reaction
Cyclohexa-2,4-dienones
Oxa-di-pi-methane rearrangement
1,3-Acyl shift
Photochemistry
 
Description A regio- and stereoselective cycloaddition of 6-chloromethyl-6-hydroxycyclohexa-2,4-dienones with benzofuran leading to dihydrobenzofuran annulated bicyclo[2.2.2]octenones having a beta,gamma-enone chromophore has been reported. Further transformation of adducts into benzannulated oxa-polyquinanes and dihydrobenzoftiran annulated bicyclo[4.2.0]octenones has also been described. (C) 2015 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2016-01-15T05:52:31Z
2016-01-15T05:52:31Z
2015
 
Type Article
 
Identifier TETRAHEDRON, 71(38)6979-6990
0040-4020
http://dx.doi.org/10.1016/j.tet.2015.07.007
http://dspace.library.iitb.ac.in/jspui/handle/100/17862
 
Language en