An Efficient Synthesis of Enantiopure (2R,3R)-β-Methoxytyrosine
Shou-xin Liu and Long yi Jin present a new and effective strategy for the synthesis of β-methoxytyrosine.
An Efficient Synthesis of Enantiopure (2R,3R)-β-Methoxytyrosine: L. y. Jin, S.-x. Liu and co-workers
Synlett 2015, DOI: 10.1055/s-0034-1381048
Marine sponges are an invaluable source of bioactive compounds, including depsipeptides, which are often isolated in tiny amounts from these natural sources. For this reason, chemical synthesis is often required for producing sufficient amounts of these compounds for biological testing. Easy access to building blocks such as non-proteinogenic amino acids in non-racemic form is therefore crucial for this purpose. β-Methoxytyrosine is often present in marine-derived depsipeptides, and the existing methods for its synthesis are affected by drawbacks that limit their efficiency. Recently, Professor Shou-xin Liu from the Yanbian University (P. R. of China) has reported in Synlett a new strategy for synthesising β-methoxytyrosine in an effective manner. The method is based on the enantiocontrolled elaboration of an easily accessible starting material, such as 3-(4-hydroxyphenyl)-3-oxopropanoate.
Synthesis of enantiopure (2R,3R)-β-methoxytyrosinevergrößern
“Enantiopure β-methoxytyrosine was synthesized by a coupling approach for synthesis and aminoacylase resolution,” said professor Liu, who is confident that the method will find widespread use in the synthesis of depsipeptides incorporating this amino acid.