Stereoselective synthesis of a potent thrombin inhibitor by a novel P2-P3 lactone ring opening

…, R Boyd, PY Kim, K Gbewonyo, M Brower…

文献索引：Nelson, Todd D.; LeBlond, Carl R.; Frantz, Doug E.; Matty, Louis; Mitten, Jeffrey V.; Weaver, Damian G.; Moore, Jeffrey C.; Kim, Jaehon M.; Boyd, Russell; Kim, Pei-Yi; Gbewonyo, Kodzo; Brower, Mark; Sturr, Michael; McLaughlin, Kathleen; McMasters, Daniel R.; Kress, Michael H.; McNamara, James M.; Dolling, Ulf H. Journal of Organic Chemistry, 2004 , vol. 69, # 11 p. 3620 - 3627

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被引用次数: 33

摘要

The concise synthesis of a potent thrombin inhibitor was accomplished by a mild lactone aminolysis between an orthogonally protected bis-benzylic amine and a diastereomerically pure lactone. The lactone was synthesized by the condensation of l-proline methyl ester with an enantiomerically pure hydroxy acid, which in turn was synthesized by a highly stereoselective (> 500: 1 er) and productive (100000: 1, S/C) enzymatic reduction of an α- ...