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| Title: | Asymmetric total synthesis of Tofacitinib |
| Authors: | Marican, A.
Simirgiotis, M.J.
Santos, L.S. |
| Keywords: | CP-690,550
JAK3 inhibitor
Mitsunobu reaction
Alane reduction |
| Issue Date: | 11-Sep-2013 |
| Publisher: | PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND |
| Citation: | Source: TETRAHEDRON LETTERS Volume: 54 Issue: 37 Pages: 5096-5098 DOI: 10.1016/j.tetlet.2013.07.042 |
| Abstract: | Abstract: A novel stereoselective synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor, has been achieved starting from (5S)-5-hydroxypiperidin-2-one in 10 steps from 2 with a 9.5% overall yield. The potentiality of this synthetic route is the obtention of tert-butyl-(3S,4R)-3-hydroxy-4-methylpiperidine-1-carboxylate (6b) as a new chiral precursor involved in the synthesis of CP690,550, in a three-step reaction, without epimerizations, rather than the 5 or more steps used in described reactions to achieve this compound from analogues of 6b. (C) 2013 Elsevier Ltd. All rights reserved. |
| Description: | Marican, A (Marican, Adolfo); Santos, LS (Santos, Leonardo S). Univ Talca, Lab Asymmetr Synth, Chem Inst Nat Resources, Talca, Chile |
| URI: | http://dspace.utalca.cl/handle/1950/9391 |
| ISSN: | 0040-4039 |
| Appears in Collections: | Artículos en publicaciones ISI - Universidad de Talca
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