Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 36, Pages 8101-8109Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403069
Keywords
Synthetic methods; Asymmetric synthesis; Medicinal chemistry; Antivirus agents; Amino acids
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Funding
- Ministry of Education of China (111 Project)
- State Administration of Foreign Expert Affairs of China [111-2-07]
- program for Changjiang Scholars and Innovative Research Team in University [IRT1193]
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A practical asymmetric synthesis of 3,4-disubstituted proline derivatives has been realized with high stereoselectivity and moderate yield. The key steps involved are desymmetric ring-opening reaction of commercially available anhydrides, intramolecular Strecker reaction and thermodynamically controlled cyanide hydrolysis. Based on this methodology, the synthesis of HCV protease inhibitor Telaprevir was achieved.
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