Diastereoselective synthesis of (2R,4R)-2-aryl-4-hydroxypyrrolidine: preparation of the side chain of novel carbapenem. |
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| Authors: | T Hashihayata H Sakoh Y Goto M Hirose S Sakuraba H Imamura Y Sugimoto K Yamada H Morishima |
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| Institution: | Banyu Tsukuba Research Institute, Ibaraki, Japan. hshytatk@banyu.co.jp |
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| Abstract: | Improved synthesis of the trans-3,5-disubstituted pyrrolidin-3-ylthio side-chain of the novel carbapenem 1 was achieved via stereoselective reduction of the 1-aryl-1-butanone derivative 5 and successive intramolecular cyclization of the resulting chiral alcohol 6. The 1-aryl-1-butanone derivative 5 was obtained by a coupling reaction of protected 4-hydroxy-2-pyrrolidone with aryl-Grignard reagent. |
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