title: Synthesis of enantiopure non-natural alpha-amino acids using tert-butyl (2S)-2-[bis-(tert-butoxycarbonyl)amino]-5-oxopentanoate as key-intermediate:the first synthesis of(S)-2-amino-oleic acid.
abstract: A general method for the synthesis of enantiopure non-natural alpha-amino acids is described. The key intermediate tert-butyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate was obtained from l-glutamic acid after suitable protection and selective reduction of the gamma-methyl ester group by DIBALH. Wittig reaction of this chiral aldehyde with various ylides led to a variety of delta,epsilon-unsaturated alpha-amino acids. This methodology was applied to the synthesis of (S)-2-amino-oleic acid.
authors.affiliation: Chemical Laboratories, Agricultural University of Athens, Greece.
authors.forename: V
authors.initials: V
authors.lastname: Constantinou-Kokotou
authors.forename: V
authors.initials: V
authors.lastname: Magrioti
authors.forename: T
authors.initials: T
authors.lastname: Markidis
authors.forename: G
authors.initials: G
authors.lastname: Kokotos
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis; D018698:Glutamic Acid / Q000737:chemistry*; D009829:Oleic Acids / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D009829:Oleic Acids; D009942:Organometallic Compounds; D018698:Glutamic Acid; C088318:2-(amino)oleic acid; C035719:diisobutylaluminum