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Asymmetric Synthesis of 3,4‐Disubstituted Proline Derivatives: Application in Synthesis of Hepatitis C Virus Protease Inhibitor Telaprevir
Author(s) -
Zhang Fan,
Wen Xiaoan,
Xu QingLong,
Sun Hongbin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403069
Subject(s) - chemistry , telaprevir , strecker amino acid synthesis , proline , protease inhibitor (pharmacology) , hydrolysis , stereoselectivity , yield (engineering) , intramolecular force , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , virus , biochemistry , virology , catalysis , amino acid , genotype , gene , materials science , ribavirin , biology , antiretroviral therapy , viral load , metallurgy
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.