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.
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.
Constantinou-Kokotou
V
V
Chemical Laboratories, Agricultural University of Athens, Greece.
Magrioti
V
V
Markidis
T
T
Kokotos
G
G
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
D000596:Amino Acids; D009829:Oleic Acids; D009942:Organometallic Compounds; D018698:Glutamic Acid; C088318:2-(amino)oleic acid; C035719:diisobutylaluminum