title: Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid.
abstract: 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.
authors.affiliation: Laboratorio de Productos Naturales, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Universidad de Antofagasta 02800, Casilla 170, Antofagasta 1240000, Chile. mario.simirgiotis@uantof.cl.
authors.forename: Mario J
authors.initials: MJ
authors.lastname: Simirgiotis
authors.affiliation: Departamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, Chile. jvallejos01@ucn.cl.
authors.forename: Javier
authors.initials: J
authors.lastname: Vallejos
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago 7800024, Chile. areche@uchile.cl.
authors.forename: Carlos
authors.initials: C
authors.lastname: Areche
authors.affiliation: Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Quillota 980, Viña del Mar 2520000, Chile. bsepulveda@uc.cl.
authors.forename: Beatriz
authors.initials: B
authors.lastname: Sepúlveda
mesh_terms: D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D008958:Models, Molecular; D010875:Pipecolic Acids / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011789:Quantum Theory; D013816:Thermodynamics
chemical_list: C000599697:4,5-di-hydroxy-pipecolic acid; D000598:Amino Acids, Cyclic; D001386:Azides; D010875:Pipecolic Acids; D010880:Piperidines