Asymmetric Synthesis of 3,4-Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir.

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. [ABSTRACT FROM AUTHOR]