Amino-hydroxy Compounds from 1,5-Anhydro-D-fructose

1,5-Anhydro-D-fructose (AF) 1 can now be obtained by an enzymatic degradation of starch, and its chemistry and biochemistry has recently been reviewed.1 Since AF now is available from sustainable resources, we are currently working on converting AF into potential biologically active compounds.2 Acetylation of AF yields the pyrenone 2, which can be used as a chiral starting material in different ways.

In order to prepare different amino-hydroxy compounds 6-7, we have converted 2 into the oximes 3-5. The stereoselective reductions are investigated and will be discussed.