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Synthesis of ( S )‐α‐amino oleic acid
Author(s) -
Magrioti Victoria,
ConstantinouKokotou Violetta
Publication year - 2002
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-002-0884-4
Subject(s) - phosphonate , aldehyde , oleic acid , chemistry , yield (engineering) , alcohol , amino acid , organic chemistry , saponification , wittig reaction , ylide , medicinal chemistry , catalysis , biochemistry , materials science , metallurgy
An efficient synthesis of ( S )‐α‐amino oleic acid was developed. The fully protected FA derivative was obtained in four steps starting from methyl (2 S )‐2‐[bis( tert ‐butoxycar‐bonyl)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 ω‐ethyl ester to an aldehyde in the presence of α‐methyl ester, and (iv) a Wittig reaction of the latter aldehyde with the suitable ylide. Free α‐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.