2014 |
Simirgiotis, M J; Vallejos, J; Areche, C; Sepulveda, B Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid Artículo de revista Molecules, 19 (12), pp. 19516-19531, 2014, ISSN: 1420-3049. Resumen | Enlaces | BibTeX | Etiquetas: amino analogs, derivatives, inhibitors, pipecolic piperidine, protease seeds synthesis, total @article{RN181, title = {Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid}, author = { M.J. Simirgiotis and J. Vallejos and C. Areche and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000346793200014}, doi = {10.3390/molecules191219516}, issn = {1420-3049}, year = {2014}, date = {2014-01-01}, journal = {Molecules}, volume = {19}, number = {12}, pages = {19516-19531}, 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 keywords 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.}, keywords = {amino analogs, derivatives, inhibitors, pipecolic piperidine, protease seeds synthesis, total}, pubstate = {published}, tppubtype = {article} } 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 keywords 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. |
2014 |
Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid Artículo de revista Molecules, 19 (12), pp. 19516-19531, 2014, ISSN: 1420-3049. |