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

TY - JOUR

T1 - Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

AU - Reider, Paul J.

AU - Eichen Conn, Robin S.

AU - Davis, Paul

AU - Grenda, Victor J.

AU - Zambito, Arthur J.

AU - Grabowski, Edward J.J.

PY - 1987/7/1

Y1 - 1987/7/1

N2 - 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).

AB - 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).

UR - https://www.scopus.com/pages/publications/0023219599

UR - https://www.scopus.com/pages/publications/0023219599#tab=citedBy

U2 - 10.1021/jo00391a029

DO - 10.1021/jo00391a029

M3 - Article

SN - 0022-3263

VL - 52

SP - 3326

EP - 3334

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -