π-Allyl palladium approach toward the diazabicyclo[3.2.1]octane core of the naphthyridinomycin alkaloids |
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Authors: | Grace HC Woo |
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Institution: | Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA |
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Abstract: | A novel and efficient protocol for the synthesis of the 3,8-diazabicyclo3.2.1]octane system found in the naphthyridinomycin, dnacin, and tetrazomine families of alkaloids is described. The key transformation involves an intramolecular palladium-catalyzed allylic alkylation. The cyclization proceeds smoothly under mild conditions (20 mol % Pd2dba3, 1.5 equiv DBU, 65 °C, THF, 20 min) to afford 3,8-diazabicyclo3.2.1]octanes in excellent yields (94-98%). |
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