Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine |
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Authors: | Kazutaka TakedaMasahiro Toyota |
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Institution: | Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan |
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Abstract: | Functionalized bicyclo3.2.1]octanes, -oxabicyclo-4.3.0]nonanes, 3-azabicyclo3.3.0]octanes, and 3-azabicyclo4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. α-Skytanthine, a typical 3-azabicyclo4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol. |
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Keywords: | Second generation palladium-catalyzed cycloalkenylation Bicyclo[3 2 1]octanes 3-Azabicyclo[3 3 0]octanes 3-Azabicyclo[4 3 0]nonanes α-Skytanthine |
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