1,5-Anhydro-D-Fructose as Starting Material for the Synthesis of Biological Active Compounds

1,5-Anhydro-D-fructose (AF) is a valuable chiral building block[1,2] which is available by degradation from starch by a-1,4-glucan lyase[2] and which now also can be produced by efficient synthetic proedures.[3] AF has three different functional hydroxyl groups, a pro-chiral center and a permanent pyran ring thus making selective manipulations possible. In the present work methods for stereoselective amino functionalisation at C-2 has been developed to give 2-amino-2-deoxy-1,5-anhydroalditols with manno- and gluco-configuration, respectively. The 2-acetamido-2-deoxy-1,5-anhydroglucitol has been shown to cause feeding suppression. An efficient synthesis of the important glycosidase inhibitor deoxymannojirimycin (DMJ) from AF has been achieved. Acetylation of AF gives the unsaturated ketone[2,4] which was used for preparation of the natural product Clavulazine as well as the valuable antioxidant Ascopyrone P. [1] S. M. Andersen, I. Lundt, J. Marcussen and S.Yu, Carbohydr. Res. 337, 873 (2002). [2] EU-program NEPSA (NEw Products from Starch derived Anhydro-D-fructose) under the Cell Factory of 5th Framework Program, QLK3-2001-02400 [3] I. Lundt, M. Andreassen and A. Stütz, PA 2004 01060 [4] O. Deppe, A. Glümer, K. Bucholtz, S. Yu, Carbohydr. Res. 339, 2077 (2004).