Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

Paul J. Reider, Robin S. Eichen Conn, Paul Davis, Victor J. Grenda, Arthur J. Zambito, Edward J.J. Grabowski

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Abstract

A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-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).

Original languageEnglish (US)
Pages (from-to)3326-3334
Number of pages9
JournalJournal of Organic Chemistry
Volume52
Issue number15
DOIs
StatePublished - Jul 1 1987
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Reider, P. J., Eichen Conn, R. S., Davis, P., Grenda, V. J., Zambito, A. J., & Grabowski, E. J. J. (1987). Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine. Journal of Organic Chemistry, 52(15), 3326-3334. https://doi.org/10.1021/jo00391a029