Journal
TETRAHEDRON-ASYMMETRY
Volume 28, Issue 1, Pages 105-109Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2016.11.013
Keywords
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Funding
- Ministry of Science and Technology, Taiwan (ROC) [NSC 102-2113-M-007-009-MY3]
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Tofacitinib is an efficient and selective Janus kinase 3 (JAK3) inhibitor, and is used as an immunosuppressant drug for the treatment of rheumatoid arthritis and transplant patients. Herein we report a concise formal asymmetric synthesis of tofacitinib from homochiral 1,3-dioxolanone 10b, which was elaborated through a highly stereoselective Michael addition followed by solvent-free removal of the chiral auxiliary and ring cyclization to furnish chiral imide 8. The preparation of tofacitinib's precursor 16 could be obtained after reduction of 8 followed by sequential oxidation, reductive amination and SNAr reactions. (C) 2016 Elsevier Ltd. All rights reserved.
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