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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 contro... Full description

Journal Title: European Journal of Organic Chemistry December 2014, Vol.2014(36), pp.8101-8109
Main Author: Zhang, Fan
Other Authors: Wen, Xiaoan , Xu, Qing‐Long , Sun, Hongbin
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201403069
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recordid: wj10.1002/ejoc.201403069
title: Asymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
format: Article
creator:
  • Zhang, Fan
  • Wen, Xiaoan
  • Xu, Qing‐Long
  • Sun, Hongbin
subjects:
  • Synthetic Methods
  • Asymmetric Synthesis
  • Medicinal Chemistry
  • Antivirus Agents
  • Amino Acids
ispartof: European Journal of Organic Chemistry, December 2014, Vol.2014(36), pp.8101-8109
description: 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. 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.
language: eng
source:
identifier: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201403069
fulltext: fulltext
issn:
  • 1434-193X
  • 1434193X
  • 1099-0690
  • 10990690
url: Link


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titleAsymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
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subjectSynthetic Methods ; Asymmetric Synthesis ; Medicinal Chemistry ; Antivirus Agents ; Amino Acids
descriptionA 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. 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.
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titleAsymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
descriptionA 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. 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.
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titleAsymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
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atitleAsymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
jtitleEuropean Journal of Organic Chemistry
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abstractA 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. 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.
copWeinheim
pubWILEY‐VCH Verlag
doi10.1002/ejoc.201403069
pages8101-8109
date2014-12