%0 Journal Article %1 RN181 %A Simirgiotis, M.J. %A Vallejos, J. %A Areche, C. %A Sepulveda, B. %D 2014 %J Molecules %K 1-deoxygalactonojirimycin, acid, acids, amino analogs, derivatives, dqcauchile inhibitors, pipecolic piperidine, protease seeds synthesis, total %N 12 %P 19516-19531 %R 10.3390/molecules191219516 %T Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid %U /brokenurl#<Go to ISI>://WOS:000346793200014 %V 19 %X 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.

@article{RN181, 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.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Simirgiotis, M.J. and Vallejos, J. and Areche, C. and Sepulveda, B.}, biburl = {https://www.bibsonomy.org/bibtex/269ae1138418abbb9e3bd2b7a5c405f22/dqcauchile}, doi = {10.3390/molecules191219516}, interhash = {1383f05fe6deb21fff824fb76ffb37d3}, intrahash = {69ae1138418abbb9e3bd2b7a5c405f22}, issn = {1420-3049}, journal = {Molecules}, keywords = {1-deoxygalactonojirimycin, acid, acids, amino analogs, derivatives, dqcauchile inhibitors, pipecolic piperidine, protease seeds synthesis, total}, number = 12, pages = {19516-19531}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000346793200014}, volume = 19, year = 2014 }