Synthesis of (S)-alpha-amino oleic acid.
An efficient synthesis of (S)-alpha-amino oleic acid was developed. The fully protected FA derivative was obtained in four steps starting from methyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate. These steps are (i) olefination of the starting aldehyde with the appropriate phosphonate anion, (ii) hydrogenation of the double bonds, (iii) controlled reduction of omega-ethyl ester to an aldehyde in the presence of alpha-methyl ester, and (iv) a Wittig reaction of the latter aldehyde with the suitable ylide. Free alpha-amino oleic acid was prepared after deprotection of the amino group followed by saponification in a total yield of 24%. N-tert-Butoxycarbonyl-protected amino oleic acid and the corresponding amino alcohol were prepared in high yield. The structures of the products have been established by various spectroscopic techniques.
Magrioti
Victoria
V
Chemical Laboratories, Agricultural University of Athens, Greece.
Constantinou-Kokotou
Violetta
V
D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D019301:Oleic Acid / Q000138:chemical synthesis* / Q000737:chemistry
D019301:Oleic Acid