Polyoxamic acid lactone

The sulfinimine-mediated asymmetric Strecker reaction was developed by F.A. Davis et al. This method involves the addition of ethylaluminumcyanoisopropoxide to functionalized sulfinimines and the resulting diastereomeric a-amino nitriles are easily separated. Subsequent hydrolysis directly affords the enantiopure a-amino acids. This protocol was applied for the synthesis of polyoxamic acid lactone. ... 

Davis, F. A., Prasad, K. R., Carroll, P. J. Asymmetric Synthesis of Polyhydroxy a-Amino Acids with the Sulfinimine-Mediated Asymmetric Strecker Reaction 2-Amino 2-Deoxy L-Xylono-1,5-lactone (Polyoxamic Acid Lactone). J. Org. Chem. 2002, 67, 7802-7806. 

Aziridine lactone 235 (Scheme 3.87) underwent ring-opening with allyl alcohol to give a 53% yield of a-amino lactone 236, which was successfully transformed to the unnatural enantiomer of polyoxamic acid (—)-237 [32],... 

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