relation: http://d-scholarship-dev.library.pitt.edu/19907/ title: π-Allyl palladium approach toward the diazabicyclo[3.2.1]octane core of the naphthyridinomycin alkaloids creator: Woo, GHC creator: Kim, SH creator: Wipf, P description: 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%). © 2006 Elsevier Ltd. All rights reserved. date: 2006-11-06 type: Article type: PeerReviewed format: text/plain language: en rights: attached identifier: http://d-scholarship-dev.library.pitt.edu/19907/1/licence.txt identifier: Woo, GHC and Kim, SH and Wipf, P (2006) π-Allyl palladium approach toward the diazabicyclo[3.2.1]octane core of the naphthyridinomycin alkaloids. Tetrahedron, 62 (45). 10507 - 10517. ISSN 0040-4020 relation: 10.1016/j.tet.2006.06.114