Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

Molecules

Mario J. Simirgiotis²  Javier Vallejos⁴  Carlos Areche¹  Beatriz Sepúlveda³ 

[1]Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago 7800024, Chile

[2] E-Mail:

[3]Laboratorio de Productos Naturales, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Universidad de Antofagasta 02800, Casilla 170, Antofagasta 1240000, Chile

[4]Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Quillota 980, Viña del Mar 2520000, Chile

[5] E-Mail:

[6]Departamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, Chile

[7] E-Mail:

关键词: pipecolic acid;    total synthesis;    piperidine;    amino acids;   

DOI  :  10.3390/molecules191219516

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.