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An enantioselective synthesis of D-(-)-2-amino-5-phosphonopentanoic acid

An enantioselective synthesis of D-(-)-2-amino-5-phosphonopentanoic acid. Ornstein, Paul L. (Lilly Res. Lab., Eli Lilly and Co., Indianapolis, IN 46285, USA).In this study，66498-59-7 is also used. J. Org. Chem., 54(9), 2251-3 (English) 1989. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 29 (Organometallic and Organometalloidal Compounds) An enantioselective synthesis of the potent and selective N-methyl-D-aspartic acid receptor antagonist D-(-)-2-amino-5-phosphonopentanoic acid (I) was achieved in five steps and 8% overall yield. Thus, oxazinone II was metalated with Na bis(trimethylsilyl)amide, followed by alkylation with trans-BrCH2CH:CHPO3Et2 to give 1 diastereomer of the product (III). Ring opening of III with Me3SiBr, followed by hydrogenation, gave I. .