Grace H. C. Woo, Se-Ho Kim, P. Wipf
Nov 6, 2006
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
A novel and efficient protocol for the synthesis of the 3,8-diazabicyclo[3.2.1]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-diazabicyclo[3.2.1]octanes in excellent yields (94–98%).