Asymmetric Synthesis of 3, 4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir. Issue 36 (31st October 2014)

• Record Type: Journal Article
• Authors: Zhang, Fan; Wen, Xiaoan; Xu, Qing‐Long; Sun, Hongbin
• Is Part Of: European journal of inorganic chemistry. Issue 36(2014)
• Page Start: 8101
• Page End: 8109
• Publication Date: 2014-10-31
• Subjects: Synthetic methods -- Asymmetric synthesis -- Medicinal chemistry -- Antivirus agents -- Amino acids; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201403069
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract: 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 : Asymmetric synthesis of 3, 4‐disubstituted proline derivatives was developed through asymmetric ring opening of substituted anhydrides, intramolecular Strecker reaction, and thermodynamically controlled cyanide hydrolysis with high stereoselectivity and moderate yield. HCV protease inhibitor Telaprevir was synthesized by using the above methodology.