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

Molecules. 2011 Sep 7;16(9):7691-705. doi: 10.3390/molecules16097691.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Pyrimidinones / chemical synthesis*
  • Pyrimidinones / chemistry
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Amino Acids
  • Bridged Bicyclo Compounds, Heterocyclic
  • Pyrimidinones