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Novel and efficient synthesis of bicyclo[2.2.2]octenones and sigmatropic shifts in ground and excited states: Stereoselective route to cis-decalins and diquinane frameworks

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Title Novel and efficient synthesis of bicyclo[2.2.2]octenones and sigmatropic shifts in ground and excited states: Stereoselective route to cis-decalins and diquinane frameworks
 
Creator SINGH, V
IYER, SR
MOBIN, SM
 
Subject diels-alder reaction
sponge agelas-nakamurai
masked o-benzoquinones
marine sponge
natural-products
enantioselective synthesis
radical cyclization
ring-system
photochemistry
rearrangement
 
Description A new and efficient synthesis of a variety of highly embellished bicyclooctenones having an endo-vinyl moiety and their sigmatropic shifts in ground and excited states leading to a stereoselective route to substituted cis-decalins and diquinane frameworks have been described. Functionalized bicyclo[2.2.2]octenones having an endo-vinyl group and a beta,gamma-enone chromophore were prepared by in situ generation of 6-chloromethyl-6-hydroxycyclohexadienones and cycloaddition with butadiene (also generated in situ) followed by manipulation of the adducts. The presence of contiguous carbonyl, hydroxyl, and chloromethyl groups in adducts led to the introduction of various alkyl groups a to the ketone in a stereoselective fashion. The 3,3-sigmatropic shift in the bridged bicyclic compounds gave the corresponding cis-decalins, whereas the triplet sensitized irradiation led to the formation of diquinanes as a result of a 1,2-acyl shift.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T14:05:17Z
2011-12-26T12:48:25Z
2011-12-27T05:37:37Z
2011-07-14T14:05:17Z
2011-12-26T12:48:25Z
2011-12-27T05:37:37Z
2005
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 70(3), 973-981
0022-3263
http://dx.doi.org/10.1021/jo048320e
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3976
http://hdl.handle.net/10054/3976
 
Language en