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Studies on cycloaddition of cyclohexa-2,4-dienones and transformation of adducts: A general, stereoselective route to multifunctional bicyclo [2.2.2] octanes and diquinanes

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Title Studies on cycloaddition of cyclohexa-2,4-dienones and transformation of adducts: A general, stereoselective route to multifunctional bicyclo [2.2.2] octanes and diquinanes
 
Creator SINGH, V
CHANDRA, G
MOBIN, SM
 
Subject diels-alder reaction
enantioselective total-synthesis
natural-products
phenol dearomatization
asymmetric-synthesis
periodate oxidation
building-blocks
construction
prostacyclin
efficient
diels-alder reaction
photochemistry
pericyclic reaction
rearrangements
 
Description The cycloaddition of in situ generated cyclohexa-2,4-dienones with vinyl ethers, vinyl acetate, and phenyl vinyl sulfone leading to variously functionalized bicyclo[2.2.2]octanes has been examined. Functional group manipulation in the resulting adducts gave bicyclo [2.2.2] octanes endowed with a beta,gamma-enone chromophore. Triplet-sensitized irradiation of bicyclooctenones followed by reductive cleavage provided a stereoselective route to diquinane frameworks having diverse functionalities.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2011-07-30T08:44:33Z
2011-12-26T12:52:45Z
2011-12-27T05:39:37Z
2011-07-30T08:44:33Z
2011-12-26T12:52:45Z
2011-12-27T05:39:37Z
2008
 
Type Article
 
Identifier SYNTHESIS-STUTTGART, (17), 2719-2728
0039-7881
http://dx.doi.org/10.1055/s-2008-1067203
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7906
http://hdl.handle.net/10054/7906
 
Language en