Stereoselective synthesis of the nonproteinogenic amino acid (2S,3R)-3-amino-2-hydroxydecanoic acid from (4S,5S)-4-formyl-5-vinyl-2-oxazolidinone.
(4S,5S)-4-Formyl-5-vinyl-2-oxazolidinone (4b), which is readily obtained via a zinc-silver-mediated reductive elimination of alpha-d-lyxofuranosyl phenyl sulfone (3b), is successfully converted to the naturally occurring, nonproteinogenic amino acid (2S,3R)-3-amino-2-hydroxydecanoic acid (2). Also in this study, a facile "oxazolidinone rearrangement" reaction is uncovered during the attempted formation of the (methylthio)thiocarbonate derivative of the oxazolidinone alcohol 7.
Wee
Andrew G H
AG
Department of Chemistry and Biochemistry, University of Regina, Regina, Saskatchewan, S4S 0A2, Canada. andrew.wee@uregina.ca
McLeod
Douglas D
DD
D000596:Amino Acids / Q000138:chemical synthesis*; D021542:Amino Acids, Neutral / Q000138:chemical synthesis*; D002384:Catalysis; D003652:Decanoic Acids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D023303:Oxazolidinones / Q000737:chemistry*; D012834:Silver; D013237:Stereoisomerism; D015032:Zinc
C481902:3-amino-2-hydroxydecanoic acid; C481903:3-benzyl-4-formyl-5-vinyl-2-oxazolidinone; D000596:Amino Acids; D021542:Amino Acids, Neutral; D003652:Decanoic Acids; D007202:Indicators and Reagents; D023303:Oxazolidinones; D012834:Silver; D015032:Zinc