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:	Creators Email Pitt Username ORCID Woo, GHC Kim, SH Wipf, P pwipf@pitt.edu PWIPF
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:	22 Jun 2021 16:55
URI:	http://d-scholarship.pitt.edu/id/eprint/19907

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