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Cycloaddition between electron-deficient pi-systems, photochemical and radical-induced reactions: a novel, general, and stereoselective route to polyfunctionalized bridged bicyclo[2.2.2]octanes, bicyclo[3.3.0]octanes, bicyclo[4.2.0]octanes, and tricyclo[4.3.1.0(3,7)]decanes

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Title Cycloaddition between electron-deficient pi-systems, photochemical and radical-induced reactions: a novel, general, and stereoselective route to polyfunctionalized bridged bicyclo[2.2.2]octanes, bicyclo[3.3.0]octanes, bicyclo[4.2.0]octanes, and tricyclo[4.3.1.0(3,7)]decanes
 
Creator SINGH, V
PAL, S
MOBIN, SM
 
Subject diels-alder reaction
enantioselective total-synthesis
organic-synthesis
natural-products
cyclization reactions
michael addition
building-blocks
beta,gamma-unsaturated ketones
enantiospecific synthesis
cyclohexadienone ketals
 
Description A novel, general, and stereoselective route to functionalized bridged bicyclo[2.2.2]octanes, bicyclo[3.3.0]octanes, bicyclo[4.2.0]octanes, and tricyclo[4.3.1.0(3.7)]decanes has been described. Various functionalized and sustituted bicyclo[2.2.2]octanes endowed with beta,gamma-enone chrornophore were synthesized via cycloaddition of in situ generated cyclohexa-2,4-dienones with electron-deficient 2 pi partners and manipulation of the resulting adducts. Triplet sensitized irradiation of bridged bicyclooctenones led to synthesis of bicyclo[3.3.0]octanoids, whereas the direct irradiation furnished bicyclo [4.2.0] octanes in stereoselective fashion as a result of modulation of reactivity in excited states. Further, manipulation of the adducts led to appropriately appended and functionalized bicyclo[2.2.2]octanes that upon radical induced cyclization provided an efficient and stereoselective route to the tricyclo[4.3.1.0(3.7)]decane (isotwistane) framework of pupukeananes.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-10-14T00:00:59Z
2011-12-15T09:16:16Z
2011-10-14T00:00:59Z
2011-12-15T09:16:16Z
2006
 
Type Review
 
Identifier JOURNAL OF ORGANIC CHEMISTRY,71(8)3014-3025
0022-3263
http://dx.doi.org/10.1021/jo052544v
http://dspace.library.iitb.ac.in/xmlui/handle/10054/13886
http://hdl.handle.net/100/3084
 
Language en