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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/3084

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[,7)]decanes
Authors: SINGH, V
Issue Date: 2006
Citation: JOURNAL OF ORGANIC CHEMISTRY,71(8)3014-3025
Abstract: 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[]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[]decane (isotwistane) framework of pupukeananes.
URI: http://dx.doi.org/10.1021/jo052544v
ISSN: 0022-3263
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