Amino sugars total synthesis

In a total synthesis of inhibitors of this kind, the following methods have so far been employed successfully (a) reaction of a cyclohexenyl halide with an amine, (b) coupling of an amine with an epoxide, and (c) condensation of an amine with ketone and reduction of the resulting Schiff base (reductive alkylation of an amino sugar). 

For the total synthesis of aminodeoxy sugars from nonsugar precursors, it is logical to turn to amino acids as primary sources of chiral templates. The challenge is to find innovative and stereocontrolled methods of chain extension reactions that lead to higher-carbon aminodeoxy sugars. 

The main purpose of this chapter is to present the basic transformations leading t< chirons useful in the total synthesis of amino sugars. Although the interest in the applicatioi of a-amino acids in the total synthesis of natural products has a long tradition, only the pas 10-15 years brought impressive expansion in this field [3-5]. The subject of total synthesi... 

A. Golfbiowski and J. Jurczak, a-Amino-P-hydroxy acids in the total synthesis of amino sugars, Synlett p. 241 (1993). 

In the late 1960s and into the mid-1970s new synthetic reports appeared in the literature. Most of these focused on the total synthesis of naturally occurring pyranosyl sugar amino acid conjugates. Then, in 1976, Fuchs and Lehmann published the first synthesis of sugar amino acids amidically linked in a fashion similar to a-amino acids. Surprisingly, this disclosure received little attention for nearly 20 years. 

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