Synthesis and transformations of di-endo-3-aminobicyclo-[2.2.2]oct-5-ene-2- carboxylic acid derivatives

Márta Palkó, Pál Sohár, Ferenc Fülöp

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and allendo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or γ-lactone intermediates by the stereoselective functionalization of an Nprotected derivative of endo-3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylic acid (2). Ring closure of β-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.

Original languageEnglish
Pages (from-to)7691-7705
Number of pages15
JournalMolecules
Volume16
Issue number9
DOIs
Publication statusPublished - Sep 1 2011

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Keywords

  • Cyclization
  • Heterocycles
  • Hydroxy-β-amino acids
  • Microwave
  • Retro Diels-Alder reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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