Synthesis of (R)-serine-2-d and its conversion to the broad-spectrum antibiotic fludalanine

PJ Reider, RSE Conn, P Davis, VJ Grenda…

Index: Reider; Eichen Conn; Davis; et al. Journal of Organic Chemistry, 1987 , vol. 52, # 15 p. 3326 - 3334

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Citation Number: 36

Abstract

A novel and practical synthesis of (R)-serine-gd that is stoichiometric in its use of deuterium is described. Isopropyl (R, S)-2-phenyl-2-oxaoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (> 99.8%) unnatural amino acid with> 98% isotopic purity. Fluorination of the primary hydroxyl with SF4 produces (S)-3- fluoroalanine-2-d (Fludalanine).

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Synthesis of (R)-serine-2-d and its conversion to the broad-spectrum antibiotic fludalanine

[Journal of Organic Chemistry, , vol. 52, # 15 p. 3326 - 3334]

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