While the synthesis of non-natural amino acids has been a vibrant field, not all of the developed syntheses are straightforward, accessible or applicable to a broad range of amino acids.  The chiral pool approach generates the chirality of the amino acid from a natural source and can streamline the syntheses if chosen appropriately.

 

The Serine-lactone can be generated in one step from protected serine and serve as a versatile intermediate in the synthesis of non-natural amino acids. The nucleophilic opening of this lactone will be studied using different nucleophiles to synthesize non-natural amino acids as well as to gain insight into the factors that control the selectivity in the ring opening.

references:
(a) Arnold, L.D.; Kalantar, T.H.; Vederas, J.C. J.Am. Chem. Soc. 1985, 107, 7105-7109.
(b) Arnold, L.D.; Drover, J.C.G.; Vederas, J.C. J. Am. Chem. Soc. 1987, 109, 4649-4659.