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π-Allyl palladium approach toward the diazabicyclo[3.2.1]octane core of the naphthyridinomycin alkaloids

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

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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%). © 2006 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Woo, GHC
Kim, SH
Wipf, Ppwipf@pitt.eduPWIPF
Date: 6 November 2006
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 62
Number: 45
Page Range: 10507 - 10517
DOI or Unique Handle: 10.1016/j.tet.2006.06.114
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 30 Oct 2013 16:56
Last Modified: 05 Feb 2019 03:55
URI: http://d-scholarship.pitt.edu/id/eprint/19907

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