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Molecules 2011, 16(9), 7691-7705; doi:10.3390/molecules16097691
Article

Synthesis and Transformations of di-endo-3-Aminobicyclo-[2.2.2]oct-5-ene-2-carboxylic Acid Derivatives

1, 2 and 1,*
1 Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary 2 Institute of Chemistry, Eötvös Lóránd University, H-1518 Budapest, POB 32, Hungary
* Author to whom correspondence should be addressed.
Received: 18 July 2011 / Revised: 24 August 2011 / Accepted: 6 September 2011 / Published: 7 September 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and all-endo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or g-lactone intermediates by the stereoselective functionalization of an N-protected derivative of endo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid (2). Ring closure of b-amino ester 4 resulted in tricyclic pyrimidinones 15 and 16. The structures, stereochemistry and relative configurations of the synthesized compounds were determined by IR and NMR.
Keywords: hydroxy-b-amino acids; cyclization; heterocycles; retro Diels-Alder reaction; microwave hydroxy-b-amino acids; cyclization; heterocycles; retro Diels-Alder reaction; microwave
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Palkó, M.; Sohár, P.; Fülöp, F. Synthesis and Transformations of di-endo-3-Aminobicyclo-[2.2.2]oct-5-ene-2-carboxylic Acid Derivatives. Molecules 2011, 16, 7691-7705.

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