RESUMO

An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-di-hydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS) and computational analysis.

Assuntos

Aminoácidos Cíclicos/química , Aminoácidos Cíclicos/síntese química , Química Orgânica/métodos , Ácidos Pipecólicos/química , Azidas/química , Catálise , Modelos Moleculares , Piperidinas/síntese química , Piperidinas/química , Teoria Quântica , Termodinâmica