A β-Lactone Route to Chiral γ-Substituted α-Amino Acids: Application to the Concise Synthesis of ( S)- α-Azidobutyro Lactone and a Natural Amino Acid
2002; American Chemical Society; Volume: 4; Issue: 4 Linguagem: Inglês
10.1021/ol017120b
ISSN1523-7060
AutoresReginald L. Tennyson, Guillermo S. Cortez, Héctor J. Galicia, Charles R. Kreiman, Christina M. Thompson, Daniel Romo,
Tópico(s)Carbohydrate Chemistry and Synthesis
Resumoβ-Lactones are useful synthetic intermediates allowing access to a number of functional arrays. In this report, enantiomerically pure 4-trichloromethyl-2-oxetanone is shown to be a versatile amino acid synthon leading to a variety of γ-substituted α-amino acid precursors. The utility of this methodology was demonstrated by the concise synthesis of a protected homoserine equivalent, α-azidobutyro lactone, and a naturally occurring α-amino acid from the seeds of Blighia unijugata.
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