α-Amino-β-hydroxy Acids in the Total Synthesis of Amino Sugars

The use of suitably protected serine- and threonine-derived aldehydes as chirons offers many new possibilities in stereocontrolled synthesis of amino sugars. The application of these chirons to various reactions such as metalloorganic addition, [4+2] cycloaddition, and cyclocondensation enabled the development of a unique methodology for highly controlled formation of new chiral centers. For illustration of this methodology, a survey of total synthesis of selected, naturally occurring amino sugars is presented. 1. Introduction 2. Developed Methodology: Scope and Limitations 3. Practical Tests of the Developed Methodology: Total Syntheses of Selected Amino Sugars 4. Conclusion