Synthesis of Diepoxides and Diaziridines, Precursors of Enantiomerically Pure a-Hydroxy and a-Amino Aldehydes or Acids, from D-Mannitol

Abstract

Specific activations or protections of the hydroxyl groups of 3-4-0-isopropylidene-D-mannitol 2 followed by intramolecular SN2 reactions, lead to the chiral diepoxides 9 and 1 and to the chiral diaziridines 2 and 2 precursors of enantiomerically pure a-hydroxy and u-amino aldehydes or acids.E n a n t i o m e r i c a l l y p u r e a -h y d r o x y a l d e h y d e s o r a c i d s and a-aminoaldehydes or acids are key intermediates for the synthesis of biologically active compounds a s arachidonic acid metabolites.peptides analogues.These intermediates can be obtainedlS2 from a u n i q u e , i n e x p e n s i v e , c h i r a l , n a t u r a l l y o c c u r r i n g c o m pound, D-mannitol, according to the following scheme: CHO COOH Nu Nu COOH