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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[188.8.131.52(3,7)]decanes|
|Publisher:||AMER CHEMICAL SOC|
|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[184.108.40.206(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[220.127.116.11(3.7)]decane (isotwistane) framework of pupukeananes.|
|Appears in Collections:||Review|
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