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

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

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 Molecular Diversity)
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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
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MDPI and ACS Style

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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