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Synlett 1999; 1999(S1): 909-912
DOI: 10.1055/s-1999-3111
DOI: 10.1055/s-1999-3111
letter
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Trials for the Synthesis of (R)-4-Mercapto-pyrrolidin-2-one ((R)-MPD)
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Publication History
Publication Date:
31 December 1999 (online)
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Several trials were made for the syntheses of (S)-4-hydroxy-pyrrolidin-2-one ((S)-HPD) and (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD), a substituent at the 2-position of the orally active carbapenem antibiotic CS-834. The latter was synthesized from prochiral dimethyl or diethyl 3-p-methoxybenzylthioglutarate using pig liver esterase technology to give monoester with an optical purity of 51-71% e.e. as a key intermediate.
γ-lactam formation - 4-mercapto-pyrrolidone - pig liver esterase - intramolecular Schmidt reaction - Curtius rearrangement - 4-hydroxy-pyrrolidone - CS-834