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.

摘要

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.