Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid
© 2014 by the authors; licensee MDPI, Basel, Switzerland. An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-dihydroxy-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.
Artículo de publicación SCOPUS
Quote ItemMolecules, Volumen 19, Issue 12, 2018, Pages 19516-19531